Hydrochloric Acid → HCID 85517007, compound

HRID 2274584Notes

Reaction equation

HRID 2274584 reaction equation
[CH2:1]([N:5]([CH2:51][CH2:52][CH2:53][CH3:54])[C:6]([C:8]1[CH:12]=[C:11]([CH3:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:16][C:15]=2[C:30]([N:32]2[C@H:41]([CH2:42][O:43][Si](C(C)(C)C)(C)C)[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])[N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].C(N(CCCC)C(C1C=C(C)N(C2C=CC(N(S(C3C=CC=CC=3)(=O)=O)S(C3C=CC=CC=3)(=O)=O)=CC=2C(N2[C@H](CO[Si](C(C)(C)C)(C)C)CC3C(=CC=CC=3)C2)=O)N=1)=O)CCC.Cl.C([O-])(O)=O.[Na+]>C1COCC1.O>[CH2:51]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:8]1[CH:12]=[C:11]([CH3:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:22])=[O:23])=[CH:16][C:15]=2[C:30]([N:32]2[CH:41]([CH2:42][OH:43])[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])[N:9]=1)=[O:7])[CH2:52][CH2:53][CH3:54]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131733393HCID 131733393, compoundHCID 131733394HCID 131733394, compound

Product 1

HCID 85517007HCID 85517007, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)—N,N-dibutyl-1-(2-(3-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(phenylsulfonamido)phenyl)-5-methyl-1H-pyrazole-3-carboxamide and (S)—N,N-dibutyl-1-(2-(3-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(N-(phenylsulfonyl)phenylsulfonamido)phenyl)-5-methyl-1H-pyrazole-3-carboxamide (0.21 g, 0.272 mmol) in THF (2.1 mL) was treated with 3N HCl (0.62 mL) at RT for 10 min. The reaction mixture was diluted with water (20 mL), the pH was adjusted to about 8 using aq. NaHCO3 solution and extracted with EtOAc (100 mL). The organic layer was washed with water (50 mL), brine (50 mL), dried over sodium sulphate and concentrated invacuo. The residue was purified on silica gel (100-200 mesh) to afford the title compound as a hygroscopic solid, 0.025 g (14%). Rf=0.38 (5% MeOH in DCM); 1H NMR (400 MHz, DMSO-d6): δ 10.85-10.70 (m, 1H, D2O exchangeable), 7.78-6.60 (m, 12H), 6.50-6.20 (m, 1H), 5.00-3.60 (m, 4H), 3.60-2.40 (m, 8H), 2.25-2.00 (m, 3H), 1.60-0.50 (m, 14H); LC-MS: m/z 658.4 (M+H), HPLC: 95.08% (RT=9.403 min., method I).

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. washThe organic layer was washed with water (50 mL), brine (50 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated invacuo
  5. customThe residue was purified on silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-05e133b3c1dd4c7db186f4cd4f9be124
Source dataset
uspto-grants-2015_09
Patent number
US09126980B2

Reaction notes

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