Sodium Hydroxide → HCID 67388769, compound

HRID 908493Notes

Reaction equation

[OH-].[Na+].[NH2:3][C:4]1[C:9]([C:10]2[O:11][C:12]3[C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:8][C:7]([C:23]2[CH:24]=[N:25][N:26]([CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)[CH:27]=2)=[CH:6][N:5]=1>CO>[NH2:3][C:4]1[C:9]([C:10]2[O:11][C:12]3[C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:8][C:7]([C:23]2[CH:24]=[N:25][N:26]([CH:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33]3)[CH:27]=2)=[CH:6][N:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A 3N aqueous solution of sodium hydroxide (0.694 ml) was added to methyl 2-[2-amino-5-[1-(1-tert-butoxycarbonyl-4-piperidyl)pyrazol-4-yl]-3-pyridyl]-1,3-benzoxazole-7-carboxylate (360 mg) dissolved in methanol (5 ml). The resulting solution was heated at 50° C. for 2 hours. The mixture was evaporated to dryness. Water (30 ml) was added and the pH was adjusted to 5 with dilute hydrochloric acid. The resultant solid was filtered, washed with water and dried under reduced pressure to afford 2-[2-amino-5-[1-(1-tert-butoxycarbonyl-4-piperidyl)pyrazol-4-yl]-3-pyridyl]-1,3-benzoxazole-7-carboxylic acid (320 mg) as yellow solid. NMR Spectrum: (DMSOd6) 1.46 (s, 9H), 1.80 (dd, 1H), 1.85 (dd, 1H), 2.00-2.09 (m, 2H), 2.93 (bs, 2H), 3.98-4.12 (m, 2H), 4.35-4.44 (m, 1H), 7.52 (dd, 1H), 7.63 (bs, 2H), 7.83 (s, 1H), 7.92 (d, 1H), 8.06 (d, 1H), 8.27 (s, 1H), 8.33 (d, 1H), 8.52 (d, 1H); Mass spectrum: M+H+ 505.

Workup

customThe mixture was evaporated to dryness
additionWater (30 ml) was added
filtrationThe resultant solid was filtered
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-4e669e4fac324ac7801319952e52ba15
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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