Hydrochloric Acid → HCID 131726125, compound

HRID 856914Notes

Reaction equation

HRID 856914 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[ClH:35]>C1COCC1.C(OCC)C>[ClH:35].[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21864779HCID 21864779, compound2×

Product 1

HCID 131726125HCID 131726125, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-tert-Butyl 4-(4-{[(4-methylphenyl)sulfonyl]amino}-1-naphthyl)-1-piperazinecarboxylate (intermediate 10) (0.4 g, 0.8 mmol) was dissolved in THF (20 mL) and treated with a 1N solution of HCl in diethyl ether (30 mL) for twelve hours. The product was collected as a pale pink solid. Yield 0.2 g (60%). mp 181° C. (dec); 1H NMR (DMSO-d6) δ 2.80 (s, 3 H), 3.1 (br, 4 H), 3.3 (br, 4 H), 7.00 (q, J=8.06 Hz, 2 H), 7.27 (ab, J=8.30 Hz, 2 H), 7.4–7.5 (m, 2 H), 7.53 (ab, J=8.30 Hz, 2 H), 7.99 (d, J=8.06 Hz, 1 H), 8.07 (d, J=7.57 Hz, 1 H), 9.2 (br, 2 H); MS (ESI+) for C21 H23 N3 O2 S Found m/z 381.1499 M+. Calc. 381.1611.

Workup

  1. customThe product was collected as a pale pink solid

Sources & evidence

ORD record
ord-1609169f7b1f4720a546e63aceda04b4
Source dataset
uspto-grants-2006_12
Patent number
US07144883B2

Reaction notes

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