Hydrochloric Acid → HCID 69592669, compound

HRID 1241605Notes

Reaction equation

HRID 1241605 reaction equation
[CH2:1]([N:3]([CH2:47][CH3:48])[CH2:4][CH2:5][N:6]([C:21]([CH2:23][N:24]1[CH:29]=[C:28]([CH2:30][C:31]2[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=2)[C:27](=[O:37])[N:26]=[C:25]1[S:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=1)=[O:22])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:2].Cl.CCOCC>ClCCl>[ClH:20].[CH2:47]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]([C:21]([CH2:23][N:24]1[CH:29]=[C:28]([CH2:30][C:31]2[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=2)[C:27](=[O:37])[N:26]=[C:25]1[S:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=1)=[O:22])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[CH3:48]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 23395801HCID 23395801, compound

Product 1

HCID 69592669HCID 69592669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The free base from Example 6 (8.7 g, 1 equiv) was dissolved in dichloromethane (50 ml) and 1M hydrogen chloride in ether (1 equiv) was added dropwise under argon. The mixture was evaporated to ca. half volume and sonicated to obtain a clear solution, which was transferred to a syringe and added dropwise to ether (200 ml) with vigorous stirring. The white solid was filtered off, washed with ether and dried in vacuo; yield 8.55 g. 1H-NMR (DMSO, ca 2:1 rotamer mixture) δ 1.14–1.24 (6H,m), 3.1 (6H, m), 3.6 (2H,m), 3.76 (3H,s), 4.38/4.45 (2H,2x s), 4.61/4.70 (2H,2x s), 4.98/5.11 (2H,2x s), 6.75/6.79 (1H,2x s), 7.1–7.7 (15H,m), 10.15/10.75 (1H,2x br s; MS (APCI+) found (M+1)=687/689; C37H40ClFN6O2S requires 686/688.

Workup

  1. customThe mixture was evaporated to ca. half volume
  2. customsonicated
  3. customto obtain a clear solution, which
  4. customwas transferred to a syringe
  5. filtrationThe white solid was filtered off
  6. washwashed with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ceb0634ebd1e46d0adaace4dacfa6253
Source dataset
uspto-grants-2006_10
Patent number
US07115616B2

Reaction notes

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