N-Benzylethylenediamine → HCID 50923854, compound

HRID 570416Notes

Reaction equation

C(OC([N:8]1[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])[CH2:9]1)=O)(C)(C)C.C(NCCN)[C:32]1[CH:37]=[CH:36]C=[CH:34][CH:33]=1>>[CH2:12]([NH:8][CH2:9][CH2:10][NH:13][C:14]([C:16]1[S:17][CH:18]=[CH:19][C:20]=1[NH:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[NH:28][CH:29]=[CH:30][C:23]=12)=[O:15])[C:11]1[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=1

Participants

Reactant 2

HCID 77801N-Benzylethylenediamine

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 50923854HCID 50923854, 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 N-benzylethylenediamine instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 392 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.27 (1H, s) 8.05 (1H, t, J=5.47 Hz) 8.01 (1H, d, J=5.37 Hz) 7.77 (1H, d, J=5.37 Hz) 7.46 (1H, d, J=5.47 Hz) 7.14-7.33 (7H, m) 6.80 (1H, d, J=5.56 Hz) 6.43 (1H, dd, J=3.42, 1.85 Hz) 3.69 (2H, s) 3.35 (2H, d, J=6.05 Hz) 2.65 (2H, t, J=6.59 Hz)

Sources & evidence

ORD record: ord-ef506876997248a1a9389b1c1c0fdb4f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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