Sodium Hydroxide → 4-(4-(7-chloro-1-ethyl-1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-ylamino)phenol

HRID 1875426Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([C:11](=O)/[CH:12]=[CH:13]/N(C)C)=[CH:9][N:8]([CH2:18][CH3:19])[C:7]=12.Cl.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH2:31])=[NH:30])=[CH:24][CH:23]=1.[OH-].[Na+]>CCO.CC#N>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([C:11]3[CH:12]=[CH:13][N:31]=[C:29]([NH:28][C:25]4[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=4)[N:30]=3)=[CH:9][N:8]([CH2:18][CH3:19])[C:7]=12

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (E)-1-(7-chloro-1-ethyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one (0.5 mmol), 1-(4-hydroxyphenyl)guanidine hydrochloride (0.5 mmol) and NaOH (2 mmol) in a mixture of EtOH-MeCN (1:2, v/v, 3 mL) was heated in a microwave at 150° C. for 25 minutes. The residue was purified by column chromatography using EtOAc/PE (1:3, v/v) to yield 4-(4-(7-chloro-1-ethyl-1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-ylamino)phenol as white solid. 1H-NMR (DMSO-d6) δ: 1.43 (m, 3H, CH3), 4.49 (m, 2H, CH2), 6.74 (m, 2H, Ph-H), 7.11 (d, 1T-F=5.6 Hz, Pyrimidin-H), 7.52 (m, 2H, Ph-H), 7.74 (d, 1H, J=5.6 Hz, Ar—H), 8.10 (d, 1H, J=5.2 Hz, Ar—H), 8.29 (d, 1H J=5.6 Hz, Pyrimidin-H), 8.37 (s, 1H, Ar—H), 9.04 (s, 1H, OH), 9.09 (s, 1H, NH). MS (ESI+) m/z 362.1609 (M+H)+.

Workup

customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-f336a8a1f1f645f393f2b1bfde49a21b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309550B2

Reaction notes

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