Benzyl chloroformate → HCID 178480936, compound

HRID 51621Notes

Reaction equation

HRID 51621 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH2:18])=[N:15][CH:14]=[N:13][C:12]=3[N:11]([C@H:19]3[CH2:24][CH2:23][C@H:22]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)[CH2:21][CH2:20]3)[CH:10]=2)=[CH:5][CH:4]=1.Cl[C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34]>N1C=CC=CC=1.ClCCl>[NH2:18][C:16]1[C:17]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:33](=[O:34])[O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:8][CH:7]=3)=[CH:10][N:11]([C@H:19]3[CH2:24][CH2:23][C@H:22]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)[CH2:21][CH2:20]3)[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 178480933HCID 178480933, compound

Product 1

HCID 178480936HCID 178480936, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of trans-5-[4-(aminomethyl)phenyl]-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (50 mg, 0.119 mol) in pyridine (2 mL) and dichloromethane (2 mL) was cooled to 0° C. then treated with benzyl chloroformate (22 mg, 0.131 mmol). The mixture was warmed to ambient temperature and stirred an additional 2 hours, evaporated and the residue purified by preparative reverse-phase chromatography to give trans-benzyl N-(4-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}benzyl)carbamate: 1H NMR (DMSO-d6, 400 MHz) 8.13(s, 1H), 7.85(t, 1H), 7.3-7.42(m, 10H), 6.02(bs, 2H), 5.06(s, 2H), 4.54(m, 1H), 4.26(d, 2H), 1.44-2.37(m, 20H); RP-HPLC (Hypersil HS C18, 5 m, 100 A, 250×4.6 mm; 5%-50% acetonitrile over 25 min, 1 mL/min) tr 22.15 min.; MS:MH+ 554.3.

Workup

  1. temperatureThe mixture was warmed to ambient temperature
  2. customevaporated
  3. customthe residue purified by preparative reverse-phase chromatography

Sources & evidence

ORD record
ord-e0aaa875ef364207a7840569c648892f
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

Loading…