tert-Butyl (2-aminoethyl)(benzyl)carbamate → Benzyl-(2-{[3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-2-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester

HRID 570500Notes

Reaction equation

HRID 570500 reaction equation
ClC1C=[C:4](C=CC=1)[CH2:5][NH:6][C:7]([C:9]1[O:10][CH:11]=[CH:12][C:13]=1[NH:14][C:15]1[C:16]2[CH:23]=[CH:22][NH:21][C:17]=2[N:18]=[CH:19][N:20]=1)=[O:8].[C:27]([O:31][C:32](=[O:44])[N:33](CCN)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([CH3:30])([CH3:29])[CH3:28]>>[C:27]([O:31][C:32](=[O:44])[N:33]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH2:4][CH2:5][NH:6][C:7]([C:9]1[O:10][CH:11]=[CH:12][C:13]=1[NH:14][C:15]1[C:16]2[CH:23]=[CH:22][NH:21][C:17]=2[N:18]=[CH:19][N:20]=1)=[O:8])([CH3:30])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 2760958tert-Butyl (2-aminoethyl)(benzyl)carbamateHCID 669574393-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-2-carboxylic acid 3-chloro-benzylamide

Product 1

HCID 66958098Benzyl-(2-{[3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-2-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl esterYield 8%

Procedure

The title compound was prepared in an analogous manner as 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-2-carboxylic acid 3-chloro-benzylamide using (2-aminoethyl)-benzyl carbamic acid tert-butyl ester instead of 3-chlorobenzylamine and obtained in 8% yield (HPLC: 90%, RT: 6.60 min). 1H NMR (DMSO-d6) 11.99 (br s, 1H), 9.80 (br s, 1H), 8.44 (br s, 1H), 8.38 (s, 1H), 7.80 (br s, 1H), 7.71 (br s, 1H), 7.37 (dd, J=3.3, 2.6 Hz, 1H), 7.33 (d, J=7.3 Hz, 2H), 7.28-7.21 (m, 3H), 6.42 (br s, 1H), 4.44 (s, 2H), 3.40 (br s, 2H), 1.34 (s, 9H); MS (m/z) 477 [M+H]+.

Workup

  1. customobtained in 8% yield (HPLC: 90%, RT: 6.60 min)

Sources & evidence

ORD record
ord-135ad734d2764384b1c9e915359b441c
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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