Hydrochloric Acid → HCID 178485077, compound

HRID 2189936Notes

Reaction equation

HRID 2189936 reaction equation
[C:1]([N:3]=[C:4]([NH:34][CH3:35])[NH:5][CH2:6][CH2:7][CH2:8][C@:9]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:13]([C:14](=[O:19])[C@@H:15]([O:17][CH3:18])[CH3:16])[N:12]=[C:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[S:10]1)#[N:2].[ClH:36].[OH2:37]>CO.O1CCOCC1>[ClH:36].[F:27][C:21]1[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=1[C:11]1[S:10][C@@:9]([CH2:8][CH2:7][CH2:6][NH:5][C:4]([NH:34][CH3:35])=[N:3][C:1]([NH2:2])=[O:37])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:13]([C:14](=[O:19])[C@@H:15]([O:17][CH3:18])[CH3:16])[N:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178485042HCID 178485042, compound

Product 1

HCID 178485077HCID 178485077, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-cyano-1-(3-((S)-5-(2,5-difluorophenyl)-3-((S)-2-methoxypropanoyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propyl)-3-methylguanidine (Example 10; 130 mg, 0.26 mmol) in methanol (3 mL) was added HCl (0.65 mL of a 4 M solution in dioxane) and water (0.05 mL, 2.6 mmol). After stirring at room temperature for 16 hours, the mixture was concentrated under reduced pressure. The residue was triturated with ether to provide the product as a pale pink solid (135 mg, 94% yield). MS ESI (+) m/z 541 (M+Na) detected: 1H NMR (400 MHz, CD3OD) δ 7.66-7.61 (m, 1H), 7.49-7.46 (m, 2H), 7.42-7.37 (m, 2H), 7.34-7.28 (m, 3H), 4.79 (q, 1H, J=6.4 Hz), 3.53-3.43 (m, 2H), 3.36 (s, 3H), 3.30-3.20 (m, 1H), 2.95 (s, 3H), 2.67-2.55 (m, 1H), 2.23-2.11 (m, 1H), 1.75-1.63 (m, 1H), 1.43 (d, 3H, J=6.4 Hz).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-0016e4333b004aa5a37d1909daa7e54e
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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