1-(Phenylmethyl)-1H-indazol-5-amine → (1-Benzyl-1H-indazol-5-yl)-(6-benzyloxy-pyrido[3,4-d]pyrimidin-4-yl)-amine hydrochloride

HRID 566405Notes

Reaction equation

HRID 566405 reaction equation
[CH2:1]([O:8][C:9]1[N:19]=[CH:18][C:12]2[N:13]=[CH:14][N:15]=[C:16]([Cl:17])[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[N:25]=[CH:24]2>>[ClH:17].[CH2:30]([N:26]1[C:27]2[C:23](=[CH:22][C:21]([NH:20][C:16]3[C:11]4[CH:10]=[C:9]([O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[N:19]=[CH:18][C:12]=4[N:13]=[CH:14][N:15]=3)=[CH:29][CH:28]=2)[CH:24]=[N:25]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 2120691-(Phenylmethyl)-1H-indazol-5-amineHCID 227274286-(Benzyloxy)-4-chloropyrido[3,4-d]pyrimidine

Product 1

HCID 21266218(1-Benzyl-1H-indazol-5-yl)-(6-benzyloxy-pyrido[3,4-d]pyrimidin-4-yl)-amine hydrochlorideYield 75%

Procedure

6-Benzyloxy-4-chloro-pyrido[3,4-d]pyrimidine (0.54 g, ca. 2 mmol) and 5-amino-1-benzyl-1H-indazole (0.458 g, 2.05 mmol) were reacted according to Procedure A to give the title compound as a yellow solid (0.740 g, 1.50 mmol, 75%); δH [2H6]DMSO 11.50(1H,s), 9.00(1H,s), 8.77(1H,s), 8.16-8.33 (3H,m), 7.83(1H,d), 7.71 (1H,dd), 7.13-7.58 (10H,m), 5.69(2H,s), 5.55(2H,s); m/z (M+1+) 459.

Sources & evidence

ORD record
ord-48c8e0de7e74483aa15f75c17550578c
Source dataset
uspto-grants-2001_01
Patent number
US06174889B1

Reaction notes

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