Hydrochloric Acid → HCID 86729580, compound

HRID 2175428Notes

Reaction equation

HRID 2175428 reaction equation
C(OC(=O)[N:7]([CH2:27][C:28]1[S:29][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[N:31][N:32]=1)[C:8]1[CH:13]=[C:12]([O:14][CH2:15][C@H:16]2[CH2:18][C@@H:17]2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)[N:11]=[C:10]([CH3:26])[N:9]=1)(C)(C)C.Cl>>[C:33]([C:30]1[S:29][C:28]([CH2:27][NH:7][C:8]2[CH:13]=[C:12]([O:14][CH2:15][C@@H:16]3[CH2:18][C@H:17]3[C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[N:11]=[C:10]([CH3:26])[N:9]=2)=[N:32][N:31]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 90332142HCID 90332142, compound

Product 1

HCID 86729580HCID 86729580, compoundYield 117.8%

Procedure

15-4 (40 mg, 0.06 mmol) was treated with HCl (4 M in 1,4-dioxane) (2 mL) and the mixture was stirred at room temperature for 6 h. Then it was concentrated, diluted with water (1 mL), and adjusted to pH 11 with aq NaOH (4 N). The resulting mixture was extracted with DCM (10 mL×4) and the organic layer was dried over Na2SO4, concetrated to afford the title compound (30 mg, 93%). 1H NMR (400 MHz, MeOD) δ 8.08 (s, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.03 (d, J=8.0 Hz, 1H), 5.60 (s, 1H), 4.16 (dd, J=10.9, 6.5 Hz, 1H), 4.03 (dd, J=10.8, 7.5 Hz, 1H), 3.02 (s, 2H), 2.26 (s, 3H), 2.18 (s, 3H), 2.05-1.96 (m, 1H), 1.69 (d, J=6.2 Hz, 1H), 1.34 (s, 9H), 1.15-1.04 (m, 1H), 1.04-0.91 (m, 1H). LRMS (ES) calculated M+H for C22H28N6OS: 425.6. Found: 425.2.

Workup

  1. concentrationThen it was concentrated
  2. additiondiluted with water (1 mL)
  3. extractionThe resulting mixture was extracted with DCM (10 mL×4)
  4. dry with materialthe organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-99cc5437675c4fa5b78cac7cb5b66b29
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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