N-Benzylethylenediamine → HCID 70795643, compound

HRID 570460Notes

Reaction equation

C(OC(N1CCC(NC(C2SC=CC=2NC2C=CN=C3NC=CC=23)=O)C1)=O)(C)(C)C.[CH2:31]([NH:38][CH2:39][CH2:40][NH2:41])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[NH:42]1[C:46]2=[N:47][CH:48]=[CH:49][C:50]([NH:51][C:52]3[C:53]4[CH:63]=[CH:62][CH:61]=[CH:60][C:54]=4[S:55][C:56]=3[C:57](O)=[O:58])=[C:45]2[CH:44]=[CH:43]1>>[CH2:31]([NH:38][CH2:39][CH2:40][NH:41][C:57]([C:56]1[S:55][C:54]2[CH:60]=[CH:61][CH:62]=[CH:63][C:53]=2[C:52]=1[NH:51][C:50]1[CH:49]=[CH:48][N:47]=[C:46]2[NH:42][CH:43]=[CH:44][C:45]=12)=[O:58])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Reactant 3

HCID 77801N-Benzylethylenediamine

HCID 66957791HCID 66957791, compound

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 70795643HCID 70795643, 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 and 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-benzo[b]thiophene-2-carboxylic acid instead of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid. LCMS (ESI) 393 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.42 (1H, br. s.) 8.89 (1H, s) 8.23 (1H, t, J=5.37 Hz) 8.04 (1H, dt, J=8.07, 0.92 Hz) 7.82 (1H, d, J=5.37 Hz) 7.50 (2H, dddd, J=6.92, 5.94, 0.78, 0.61 Hz) 7.26-7.41 (3H, m) 7.08-7.25 (7H, m) 6.48 (1H, d, J=2.34 Hz) 6.03 (1H, d, J=5.42 Hz) 3.46 (2H, s) 2.46 (2H, t, J=6.20 Hz)

Sources & evidence

ORD record: ord-305c5e0a9914442894cd334862e66547
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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