HCID 71142521, compound → HCID 71142522, compound

HRID 1914034Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]2[N:37]([C:38]3[CH:43]=[CH:42][C:41]([C:44]4([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:47][CH2:46][CH2:45]4)=[CH:40][CH:39]=3)[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N:22]5[CH2:27][CH2:26][O:25][C@@H:24]([CH2:28][O:29]CC6C=CC=CC=6)[CH2:23]5)[CH:17]=4)=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1>CO.[Pd]>[NH2:1][C:2]1[C:7]([C:8]2[N:37]([C:38]3[CH:43]=[CH:42][C:41]([C:44]4([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:53])([CH3:52])[CH3:54])[CH2:45][CH2:46][CH2:47]4)=[CH:40][CH:39]=3)[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N:22]5[CH2:27][CH2:26][O:25][C@@H:24]([CH2:28][OH:29])[CH2:23]5)[CH:17]=4)=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

10% Pd/C (30 mg) was added to a solution of tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-(3-{(2R)-2-[(benzyloxy)methyl]morpholin-4-yl}phenyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate (31.5 mg, 0.0427 mmol) in MeOH (2 mL). The mixture was stirred at room temperature for 14 hours and 7.5 hours at 50° C. under hydrogen atmosphere. The catalyst was removed by filtration through a Celite pad and washed with MeOH. The combined filtrate and washings were concentrated. The residue was purified by PTLC (CHCl3/MeOH=9:1) to afford desired compound (5.2 mg, 18.8%) as pale yellow solid.

Workup

customThe catalyst was removed by filtration through a Celite pad
washwashed with MeOH
concentrationThe combined filtrate and washings were concentrated
customThe residue was purified by PTLC (CHCl3/MeOH=9:1)

Sources & evidence

ORD record: ord-a5571c8b98c5432b942299d7d005c39b
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609688B2

Reaction notes

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