Sodium Hydroxide → HCID 11641775, compound

HRID 2375828Notes

Reaction equation

C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([N:12]2[CH2:17][CH:16]=[C:15]([C:18]3[NH:36][C:21]4[N:22]=[CH:23][N:24]=[C:25]([NH:26][C:27]5[CH:35]=[CH:34][C:30]6[N:31]=[CH:32][S:33][C:29]=6[CH:28]=5)[C:20]=4[CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=1.[OH-].[Na+]>CO.O.CCOC(C)=O>[S:33]1[C:29]2[CH:28]=[C:27]([NH:26][C:25]3[C:20]4[CH:19]=[C:18]([C:15]5[CH2:16][CH2:17][N:12]([C:10]([C:6]6[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=6)[C:3]([OH:37])=[O:2])=[O:11])[CH2:13][CH:14]=5)[NH:36][C:21]=4[N:22]=[CH:23][N:24]=3)[CH:35]=[CH:34][C:30]=2[N:31]=[CH:32]1

Participants

Conditions

Temperature: 65 °C

Procedure

3-{4-[4-(Benzothiazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carbonyl}-benzoic acid methyl ester (0.624 mmol) was suspended in a mixture of MeOH (6.0 mL) and water (2.0 mL). 2 M NaOH solution (1.0 mmol) was then added to the above suspension and the reaction temperature increased to 65° C. The resulting suspension was stirred for a further period of 16 h. The mixture was allowed to reach r.t and diluted with EtOAc (30 mL) and washed with 2M NaOH (2×20 mL). The aqueous phase was then acidified by careful addition of conc. HCl solution until pH≈1. The resulting brown precipitate was then filtered and dried under vacuum affording the title compound. 1H NMR (DMSO, 400 MHz): δ=9.45(1H,s), 8.7(1H,s), 8.15(1H,d), 8.1(1H,d), 8.0(1H,s), 7.8(1H,d), 7.7 (1H, d), 7.6(1H, t), 6.9(1H, s), 6.6(1H, m), 6.35(1H, m), 4.35(1H, m), 4.1(1H, m), 3.9(1H, m), 2.6(1H, m). [MH+—CO2]=498.25.

Workup

washwashed with 2M NaOH (2×20 mL)
additionThe aqueous phase was then acidified by careful addition of conc. HCl solution until pH≈1
filtrationThe resulting brown precipitate was then filtered
customdried under vacuum

Sources & evidence

ORD record: ord-af7d75cff2754f66bca79b41faf234fc
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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