Benzyl chloroformate → HCID 54228515, compound

HRID 251502Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[C:18]3[C:17]([NH2:19])=[N:16][CH:15]=[N:14][C:13]=3[N:12]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>ClCCl.N1C=CC=CC=1>[NH2:19][C:17]1[C:18]2[C:10]([C:4]3[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([NH:1][C:26](=[O:27])[O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:3]=3)=[CH:11][N:12]([CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[C:13]=2[N:14]=[CH:15][N:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-(3-amino-4-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (40 mg, 0.124 mmol) in dichloromethane (1 ml) and pyridine (1 ml) was cooled to 0° C. and then treated with benzyl chloroformate (32 mg, 0.186 mmol) while maintaining a temperature of less than 5° C. The solution was stirred for another 1 hour at 0° C. then the solvents were removed under reduced pressure. Purification by preparative C-18 RP-HPLC then lyophilization provided benzyl N-[5-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (25 mg) as a white powder: 1H NMR (DMSO-d6, 400 MHz) δ 8.75 (s, 1H), 8.11 (s, 1H), 7.75 (s, 1H), 7.1-7.4 (m, 8H), 6.2 (bs, 2H), 5.15 (s, 2H), 5.07 (m, 1H), 3.8 (s 3H), 1.6-2.2 (m, 8H), RP-HPLC (Hypersil HyPurity Elite C18, 5 μm, 200 A, 250×4.6 mm; 25-100% acetonitrile-0.1 M ammonium acetate over 25 min, 1 ml/min) tr=18.63 min.; MS: MH+458.

Workup

temperaturewhile maintaining a temperature of less than 5° C
customthe solvents were removed under reduced pressure
customPurification by preparative C-18 RP-HPLC

Sources & evidence

ORD record: ord-f406518fa5fe48a287a866197ee9f60b
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863444B2

Reaction notes

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