4-Nitro-1,2-phenylenediamine → HCID 69320502, 화합물

HRID 2114609노트

반응식

HRID 2114609 반응식
[NH2:1][C:2]1[C:3]2[C:10]([C:11](O)=O)=[CH:9][N:8]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=1[NH2:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1>[CH:14]1([N:8]2[C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=3[C:10]([C:11]3[NH:29][C:21]4[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:20]=4[N:19]=3)=[CH:9]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 51117914-Nitro-1,2-phenylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 693198034-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid

생성물 1

HCID 69320502HCID 69320502, 화합물수율 28.8%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (ID, 12.0 g, 488 mmol), 1,2-diamino-4-nitrobenzene (11.2 g, 73.1 mmol), and HATU (26.0 g, 73.1 mmol) were combined and stirred in 242 mL of anhydrous NMP under N2 at 50° C. After 6 hrs, reaction was monitored by LCMS confirming the loss of the starting material and the formation of a new component. The reaction mixture was decant into ten 50 mL centrifuge tubes and concentrated overnight in the GeneVac. Dark brown oil was taken up in EtOAc (1.6 L) and extracted using 1.2 L H2O. The organic layer was washed with H2O (3×900 mL) and then concentrated. The residue (dark brown gum) was triturate in ˜900 mL CH2Cl2, 10.02 g of a reddish black solid was collected after filtration and vacuum drying. 1H NMR suggested it contained the coupling product plus 20-30% impurity. The solid was again taken up in 1.5 L EtOAc, washed with H2O (5×900 mL). The organic layer was concentrated and residue triturated in ˜900 mL CH2Cl2, filtered and dried to furnish 7.65 g of a yellow solid. 1H NMR and LCMS suggested the coupling product plus minor impurities (88% pure by LCMS at 210 nm, M/Z 381.5, retention time 2.3 min. with analytical HPLC method 1).

후처리

  1. customreaction
  2. customThe reaction mixture was decant into ten 50 mL centrifuge tubes
  3. concentrationconcentrated overnight in the GeneVac
  4. extractionextracted
  5. washThe organic layer was washed with H2O (3×900 mL)
  6. concentrationconcentrated
  7. customThe residue (dark brown gum) was triturate in ˜900 mL CH2Cl2
  8. custom10.02 g of a reddish black solid was collected
  9. filtrationafter filtration and vacuum
  10. customdrying
  11. washwashed with H2O (5×900 mL)
  12. concentrationThe organic layer was concentrated
  13. customresidue triturated in ˜900 mL CH2Cl2
  14. filtrationfiltered
  15. customdried

출처 및 근거

ORD 기록
ord-c1bbaa9d09de4a328bcb18197c14d33f
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07435739B2

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