Thiophene-3-boronic acid → HCID 58710044, compound

HRID 2375880Notes

Reaction equation

HRID 2375880 reaction equation
N1C=CC=C1[C:6]1[CH:7]=[C:8]([NH:12][C:13]2[C:14]3[CH:21]=[C:20]([C:22]4[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH:27]=4)[NH:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:9]=[CH:10][CH:11]=1.[S:35]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36]1>>[S:35]1[CH:39]=[CH:38][C:37]([C:6]2[CH:7]=[C:8]([NH:12][C:13]3[C:14]4[CH:21]=[C:20]([C:22]5[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:26][CH:27]=5)[NH:19][C:15]=4[N:16]=[CH:17][N:18]=3)[CH:9]=[CH:10][CH:11]=2)=[CH:36]1

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 58709794HCID 58709794, compound

Product 1

HCID 58710044HCID 58710044, compound

Procedure

The title compound was prepared following the procedure for tert-butyl 4-{4-[3-(1H-pyrrol-2-yl)phenylamino]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylate, but using 3-thienylboronic acid. 1H-NMR (CD3OD, 400 MHz): δ=1.50 (s, 9H), 2.56 (m, 2H), 3.67 (m, 2H), 4.13 (m, 2H), 6.30 (s, br, 1H), 6.66 (s, 1H), 7.37-7.42 (m, 2H), 7.47-7.50 (m, 2H), 7.63-7.66 (m, 2H), 8.01-8.02 (m, 1H), 8.23 (s, 1H). MS (ES+): m/z 474.04 [MH+]. HPLC: tR=3.58 min (ZQ2000, polar—5 min).

Workup

  1. customHPLC: tR=3.58 min (ZQ2000, polar—5 min)

Sources & evidence

ORD record
ord-ed9cfd137e51408ca6516036877926bb
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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