Dimethylamine, hydrochloride → N,N-dimethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide

HRID 1692030노트

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HRID 1692030 반응식
[S:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:4]=2[O:3]1.Cl.[CH3:15][NH:16][CH3:17].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1.CN(C)C=O.ClCCl>[CH3:15][N:16]([CH3:17])[C:11]([C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2](=[S:1])[O:3][C:4]=2[CH:10]=1)=[O:13]

참가 물질

8

반응물 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 207347702-Sulfanyl-1,3-benzoxazole-6-carboxylic acid

생성물 1

HCID 18967003N,N-dimethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

2-Thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid (Example 92B, 394 mg, 2.02 mmol), dimethylamine hydrochloride (181 mg, 2.22 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (844 mg, 2.22 mmol) were combined in tetrahydrofuran (20 mL) and dimethylformamide (2 mL). Diisopropylethylamine (1.5 mL, 8.68 mmol) was added and the mixture was stirred at ambient temperature overnight. The mixture was diluted with dichloromethane, washed with a 1 N aqueous solution of hydrochloric acid, and absorbed on silica gel. The crude mixture was purified with silica gel chromatography eluting with a gradient of methanol in dichloromethane (2-20%) to afford the title compound. MS (ESI+) m/z 222.9 (M+H)+.

후처리

  1. washwashed with a 1 N aqueous solution of hydrochloric acid
  2. customabsorbed on silica gel
  3. customThe crude mixture was purified with silica gel chromatography
  4. washeluting with a gradient of methanol in dichloromethane (2-20%)

출처 및 근거

ORD 기록
ord-8fd9e6c1d2d4409fa97702783c762dc5
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153813B2

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