3-Pyridinemethanamine → HCID 11614063, 화합물

HRID 1723957노트

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HRID 1723957 반응식
[C:1]([C:5]1[CH:6]=[C:7]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:8]([O:29][CH3:30])=[C:9]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH3:28])=[C:18]([N:20]3[CH:24]=[C:23]([C:25]([OH:27])=O)[CH:22]=[N:21]3)[CH:19]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:36][CH2:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[N:40]1[CH:41]=[CH:42][CH:43]=[C:38]([CH2:37][NH:36][C:25]([C:23]2[CH:22]=[N:21][N:20]([C:18]3[CH:19]=[C:14]([C:12](=[O:13])[NH:11][C:9]4[CH:10]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:6]=[C:7]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:8]=4[O:29][CH3:30])[CH:15]=[CH:16][C:17]=3[CH3:28])[CH:24]=2)=[O:27])[CH:39]=1

참가 물질

7

반응물 4

HCID 310183-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57559703HCID 57559703, 화합물

생성물 1

HCID 11614063HCID 11614063, 화합물수율 54.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

The above carboxylic acid (75 mg, 0.15 mmol), 3-(aminomethyl)pyridine (25 mg, 0.23 mmol) and HATU (85 mg, 0.23 mmol) were dissolved in DMF (1.5 mL). N,N-Diisopropylethylamine (78 μL, 0.45 mmol) was added and the reaction was stirred overnight. Water was added and the resulting solution was extracted with CH2Cl2 (4×30 mL). The combined organic extracts were washed with 5% LiCl solution, dried over MgSO4, filtered, and concentrated. The residue was purified by semi-prep HPLC. The product fractions were concentrated and sodium bicarbonate added. The resulting solid was collected by vacuum filtration, washed with water, and dried under vacuum at 55° C. to provide the title compound (48 mg, 54%) as white solid: mp 127-133° C.; ESI MS m/z 591 [C30H34N6O5S+H]+; HPLC>95%, tR=15.03 min.

후처리

  1. extractionthe resulting solution was extracted with CH2Cl2 (4×30 mL)
  2. washThe combined organic extracts were washed with 5% LiCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by semi-prep HPLC
  7. concentrationThe product fractions were concentrated
  8. additionsodium bicarbonate added
  9. filtrationThe resulting solid was collected by vacuum filtration
  10. washwashed with water
  11. customdried under vacuum at 55° C.

출처 및 근거

ORD 기록
ord-a2df1518511b4ceca56f99b2d99d5546
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485657B2

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