Sodium Bicarbonate → HCID 178492648, compound

HRID 1503856Notes

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:30]=[CH:29][C:13]([C:14]([N:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[O:15])=[CH:12][C:11]=1[O:31][CH3:32])#[N:2].C(=O)(O)[O-].[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]#[N:2])=[C:8]([NH:9][C:10]2[CH:30]=[CH:29][C:13]([C:14]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])=[CH:12][C:11]=2[O:31][CH3:32])[N:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of the product of Example 39D (100 mg, 0.13 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, 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 12.18 (s, 1 H), 9.60 (br, 1 H), 8.86 (s, 2 H), 8.64 (s, 1 H), 7.79-7.78 (m, 1 H), 7.77 (s, 1H), 7.72 (s, 1 H), 7.64-7.61 (m, 2 H), 7.48 (d, J=9 Hz, 1 H), 6.98 (s, 1 H), 6.57 (d, J=9 Hz, 1 H), 4.90 (s, 2 H), 3.88 (s, 3 H), 3.23-3.10 (m, 8 H). MS: 554 (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-542a23afce1b40cd9c458b177ea4721a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212192B2

Reaction notes

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