Sodium Bicarbonate → HCID 178491941, compound

HRID 1503871Notes

Reaction equation

[Cl:1][C:2]1[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:3]=1[CH2:4][C:5]1[C:10]2[N:11]=[CH:12][N:13](COCC[Si](C)(C)C)[C:9]=2[C:8]([C:22]#[N:23])=[C:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:27][C:26]=2[O:37][CH3:38])[N:6]=1.C(=O)(O)[O-:45].[Na+]>S(=O)(=O)(O)O.O>[Cl:43][C:39]1[CH:40]=[CH:41][CH:42]=[C:2]([Cl:1])[C:3]=1[CH2:4][C:5]1[C:10]2[N:11]=[CH:12][NH:13][C:9]=2[C:8]([C:22]([NH2:23])=[O:45])=[C:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:27][C:26]=2[O:37][CH3:38])[N:6]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of the product of Example 49C (80 mg, 0.13 mmol) in concentrated sulfuric acid (5 mL) at 0° C. was added water (1 mL) and the mixture was heated to 95° C. for 20 minutes. After cooling, 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 via preparative HPLC using a gradient of 10/90 to 75/25 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 12.00 (br, 1 H), 9.68 (br, 1 H), 8.62 (s, 1 H), 7.85 (d, J=8.4 Hz, 1 H), 7.73 (s, 1 H), 7.61-7.58 (m, 2 H), 7.48-7.42 (m, 1 H), 7.08 (d, J=1.2 Hz, 1 H), 6.62-6.58 (dd, J=8.4, 1.2 Hz, 1 H), 4.75 (s, 2 H), 4.23 (d, 2 H), 3.88 (s, 3 H), 3.44-3.41 (m, 8 H). MS: 525 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-c1b08c15a7c64b488b02ff0004d44f60
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212192B2

Reaction notes

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