Triethylamine → N-{1-[(3-Chloro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxamide Hydrochloride

HRID 15310노트

반응식

HRID 15310 반응식
[O:1]=[C:2]1[CH2:7][S:6][C:5]2[CH:8]=[CH:9][C:10]([C:12]([OH:14])=O)=[N:11][C:4]=2[NH:3]1.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH:23]2[C:27]3=[C:28]([Cl:36])[CH:29]=[N:30][C:31]4[CH:32]=[CH:33][C:34](=[O:35])[N:25]([C:26]=43)[CH2:24]2)[CH2:18][CH2:17]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[ClH:36].[Cl:36][C:28]1[CH:29]=[N:30][C:31]2[CH:32]=[CH:33][C:34](=[O:35])[N:25]3[CH2:24][CH:23]([CH2:22][N:19]4[CH2:18][CH2:17][CH:16]([NH:15][C:12]([C:10]5[CH:9]=[CH:8][C:5]6[S:6][CH2:7][C:2](=[O:1])[NH:3][C:4]=6[N:11]=5)=[O:14])[CH2:21][CH2:20]4)[C:27]=1[C:26]=23

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218737873-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acidHCID 577074754-[(4-Amino-1-piperidinyl)methyl]-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

생성물 1

HCID 68684829N-{1-[(3-Chloro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxamide Hydrochloride수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (for a synthesis see WO2003087098, Example 301(b)) (50 mg, 0.236 mmol), 4-[(4-amino-1-piperidinyl)methyl]-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (75 mg, 0.236 mmol) and triethylamine (0.066 ml 0.472 mmol) in DMF (2 ml) was added HATU (95 mg, 0.25 mmol) and the reaction was stirred at room temperature for 18 h. The reaction mixture was then evaporated to dryness, kept under high vacuum for 30 minutes, treated with dichloromethane and aqueous sodium bicarbonate solution and stirred vigorously for 30 minutes. The solid was filtered off, washed with water and dichloromethane and dried in vacuo to provide the free base of the title compound (100 mg, 83%).

후처리

  1. customThe reaction mixture was then evaporated to dryness
  2. waitkept under high vacuum for 30 minutes
  3. additiontreated with dichloromethane and aqueous sodium bicarbonate solution
  4. stirringstirred vigorously for 30 minutes
  5. filtrationThe solid was filtered off
  6. washwashed with water and dichloromethane
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-919d78e6ba2a4795ae0cf45a1dd111cf
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732461B2

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