Diisopropylethylamine → Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(pyrimidine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

HRID 712304

반응식

HRID 712304 반응식
[NH2:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:16])[NH:13][CH2:14][CH3:15])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)[CH:3]=1.[N:35]1[CH:40]=[CH:39][CH:38]=[N:37][C:36]=1[C:41](O)=[O:42].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:14]([NH:13][C:12]([NH:11][C:8]1[S:9][C:10]2[C:2]([NH:1][C:41]([C:36]3[N:37]=[CH:38][CH:39]=[CH:40][N:35]=3)=[O:42])=[CH:3][C:4]([C:17]3[CH:18]=[N:19][C:20]([N:23]4[CH2:28][CH2:27][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]4)=[N:21][CH:22]=3)=[CH:5][C:6]=2[N:7]=1)=[O:16])[CH3:15]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12626245Pyrimidine-2-carboxylic acidHCID 86664019Ethyl 1-(5-(7-amino-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

생성물 1

HCID 86664018Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(pyrimidine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Ethyl 1-[5-[7-amino-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (159 mg, 0.27 mmol), pyrimidine-2-carboxylic acid (64.2 mg, 0.52 mmol) and diisopropylethylamine (271 mg, 2.1 mmol) were dissolved in DMF (5 mL). The reaction was purged with N2 then HATU (197 mg, 0.5 2 mmol) was added and the reaction stirred at rt for 18 h. The DMF was removed under reduced pressure and the resulting residue diluted with water and extracted with EtOAc. During the work up a solid precipitated which was collected by filtration and dried in the vacuum oven to provide the crude product (100 mg, 66% yield).

후처리

  1. customThe reaction was purged with N2
  2. customThe DMF was removed under reduced pressure
  3. additionthe resulting residue diluted with water
  4. extractionextracted with EtOAc
  5. customDuring the work up a solid precipitated which
  6. filtrationwas collected by filtration
  7. customdried in the vacuum oven

출처 및 근거

ORD 기록
ord-b15fdc20bb2c4b498e26e18d2b3f1fef
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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