4-(2-Aminoethyl)benzenesulfonamide → HCID 50923998, compound

HRID 570401Notes

Reaction equation

C(OC(N1[CH2:12][CH2:11][CH:10]([NH:13][C:14]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[NH:28][CH:29]=[CH:30][C:23]=23)=[O:15])C1)=O)(C)(C)C.NCCC1[CH:39]=[CH:38][C:37]([S:40]([NH2:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1>>[S:40]([C:37]1[CH:38]=[CH:39][C:12]([CH2:11][CH2:10][NH:13][C:14]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[NH:28][CH:29]=[CH:30][C:23]=23)=[O:15])=[CH:35][CH:36]=1)(=[O:42])(=[O:41])[NH2:43]

Participants

Reactant 2

HCID 1696824-(2-Aminoethyl)benzenesulfonamide

HCID 669579823-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 50923998HCID 50923998, compound

Procedure

This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using 4-(2-aminoethyl)benzenesulfonamide instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 422 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (1H, br. s.) 10.31 (1H, s) 8.23 (1H, t, J=5.86 Hz) 8.02 (1H, d, J=5.37 Hz) 7.68-7.83 (3H, m) 7.48 (1H, d, J=5.47 Hz) 7.42 (2H, d, J=8.30 Hz) 7.32 (1H, d, J=2.93 Hz) 7.28 (2H, s) 6.83 (1H, d, J=5.37 Hz) 6.44 (1H, dd, J=3.51, 1.95 Hz) 3.50 (2H, q, J=7.13 Hz) 2.91 (2H, t, J=7.27 Hz)

Sources & evidence

ORD record: ord-773c2f630569444ab5cad6b145572fdd
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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