Water → HCID 178428028, compound

HRID 1503836Notes

Reaction equation

[C:1]([C:3]1[C:4]2[N:41](COCC[Si](C)(C)C)[CH:40]=[N:39][C:5]=2[C:6]([CH2:30][C:31]2[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:38])=[N:7][C:8]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[CH:12][C:11]=1[CH3:29])#[N:2].O.C(=O)(O)[O-:52].[Na+]>S(=O)(=O)(O)O>[Cl:37][C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:38])[C:31]=1[CH2:30][C:6]1[C:5]2[N:39]=[CH:40][NH:41][C:4]=2[C:3]([C:1]([NH2:2])=[O:52])=[C:8]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)=[CH:12][C:11]=2[CH3:29])[N:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of the product of Example 26B (194 mg, 0.27 mmol) in concentrated sulfuric acid (5 mL) was added water (1 mL) at 0° C. and the mixture was stirred at 95° C. for 20 minutes. After cooling to ambient temperature, water (3 mL) was added. The mixture was adjusted to pH 8-9 with saturated sodium bicarbonate solution and extracted with dichloromethane (3×20 mL). The organic layers were concentrated under vacuum 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 13.62 (br, 1 H), 11.4 (br, 1 H), 9.58 (br, 1 H), 8.66 (s, 2 H), 8.58 (s, 1 H), 7.75-7.57 (m, 3 H), 7.45 (d, J=9 Hz, 1 H), 6.78 (d, J=2.4 Hz, 1 H), 6.34 (dd, J=9, 2.4 Hz, 1 H), 4.70 (s, 2 H), 3.26-3.22 (m, 8 H), 2.23 (s, 3 H). MS: 510 (M+H+).

Workup

temperatureAfter cooling to ambient temperature
extractionextracted with dichloromethane (3×20 mL)
concentrationThe organic layers were concentrated under vacuum
customthe residue was purified via preparative HPLC

Sources & evidence

ORD record: ord-971c27d202d5473581c8ed23a9c50899
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212192B2

Reaction notes

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