Sodium Hydroxide → HCID 66549518, compound

HRID 1410076Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:38]=[CH:37][S:36][C:14]=3[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([NH:23][C:24]([C:26]4[CH:27]=[CH:28][C:29]([C:32]([O:34]C)=[O:33])=[N:30][CH:31]=4)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:38]=[CH:37][S:36][C:14]=3[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([NH:23][C:24]([C:26]4[CH:27]=[CH:28][C:29]([C:32]([OH:34])=[O:33])=[N:30][CH:31]=4)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)picolinate (80 mg, 0.15 mmol) in dioxane/H2O (60 mL/6 mL) was added NaOH (60 mg, 1.5 mol), the reaction mixture was heated to 35° C. with stirring for 1 hour, then dioxane was removed in vacuo, and the aqueous layer was adjusted to pH˜4-5 with conc. HCl, the precipitate was collected by filtration and washed with water (5 mL) and dried to afford 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)picolinic acid as brown solid (67 mg, 84.8%). 1H NMR (300 MHz, DMSO): δ 9.56 (s, 1H), 9.06 (s, 1H), 8.96 (d, 1H, J=6.3 Hz), 8.79 (s, 1H), 8.33 (dd, 1H, J1=8.1 Hz, J2=1.8 Hz), 8.07 (d, 1H, J=8.1 Hz), 7.86 (s, 1H), 7.50 (brs, 1H), 6.90 (d, 1H, J=8.7 Hz), 4.60-4.58 (brs, 1H), 3.76-3.52 (m, 10H), 2.30-2.24 (m, 1H), 2.11-2.07 (m, 1H). LC-MS: 522 [M+H]+, tR=1.31 min. HPLC: 98.03% at 214 nm, 97.82% at 254 nm, tR=3.20 min.

Workup

customdioxane was removed in vacuo
filtrationthe precipitate was collected by filtration
washwashed with water (5 mL)
customdried

Sources & evidence

ORD record: ord-d7d47a9436c642b3a2d4d5f40cc9d8b1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921383B2

Reaction notes

Loading…