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 15310ノート

反応式

HRID 15310 の反応式
[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

参加物

6

反応物 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

生成物 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 Hydrochloride収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-919d78e6ba2a4795ae0cf45a1dd111cf
出典データセット
uspto-grants-2010_06
特許番号
US07732461B2

反応ノート

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