Sodium Bicarbonate → HCID 178493692, compound

HRID 1503879Notes

Reaction equation

[C:1]([C:3]1[C:4]2[N:44](COCC[Si](C)(C)C)[CH:43]=[N:42][C:5]=2[C:6]([CH2:33][C:34]2[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:41])=[N:7][C:8]=1[NH:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[C:12]([F:30])[C:11]=1[O:31][CH3:32])#[N:2].C(=O)(O)[O-:54].[Na+]>S(=O)(=O)(O)O.O>[Cl:40][C:39]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:41])[C:34]=1[CH2:33][C:6]1[C:5]2[N:42]=[CH:43][NH:44][C:4]=2[C:3]([C:1]([NH2:2])=[O:54])=[C:8]([NH:9][C:10]2[CH:15]=[C:14]([F:16])[C:13]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[C:12]([F:30])[C:11]=2[O:31][CH3:32])[N:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of the product of Example 52D (130 mg, 0.17 mmol) in concentrated sulfuric acid (5 mL) at 0° C. was added water (1 mL) and the mixture was heated at 95° C. for 20 minutes. After cooling to ambient temperature, the mixture was diluted with water (3 mL), adjusted to pH 8-9 with saturated sodium bicarbonate solution and extracted with dichloromethane (3×20 mL). The combined organic phase was concentrated and the residue was purified by preparative HPLC using a gradient of 10/90 to 80/20 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 12.35 (s, 1 H), 9.61 (s, 1 H), 8.97 (s, 2 H), 8.66 (s, 1 H), 7.91 (s, 1 H), 7.74-7.66 (m 1 H), 7.56-7.53 (m, 2 H), 7.43-7.37 (m, 1 H), 4.77 (s, 2 H), 3.82 (s, 3 H), 3.21 (m, 8 H). MS: 562 (M+H+).

Workup

temperatureAfter cooling to ambient temperature
extractionextracted with dichloromethane (3×20 mL)
concentrationThe combined organic phase was concentrated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-0b7c9fccb384401c9574a9720ebbc674
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212192B2

Reaction notes

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