Aniline → HCID 69748887, compound

HRID 2301038Notes

Reaction equation

HRID 2301038 reaction equation
Cl.CN(C)CCCN=C=NCC.[Cl:13][C:14]1[CH:19]=[C:18]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=1[NH:32][C:33](=[O:41])[C@:34]([OH:40])([CH3:39])[C:35]([F:38])([F:37])[F:36].[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:13][C:14]1[CH:19]=[C:18]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([NH:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:30])=[CH:25][CH:24]=2)(=[O:21])=[O:22])[CH:17]=[CH:16][C:15]=1[NH:32][C:33](=[O:41])[C@:34]([OH:40])([CH3:39])[C:35]([F:38])([F:37])[F:36]

Participants

6

Reactant 3

HCID 6115AnilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54539434HCID 54539434, compound

Product 1

HCID 69748887HCID 69748887, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.195 g) was added to a solution of 4-(dimethylamino)pyridine (0.25 g), (R)-N-[2-chloro-4-(4-carboxyphenyl-sulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 121) (0.317 g) and aniline (0.075 ml) in DCM (30 ml) and the mixture was stirred for 6 days. Solvent was then removed by evaporation and the residue was partitioned between ethyl acetate (50 ml) and dilute aqueous hydrochloric acid (25 ml). The aqueous layer was further extracted with ethyl acetate (50 ml). The organic extracts were combined, washed with brine and dried. Volatile material was removed by evaporation and the residue was purified by chromatography eluting with 40% ethyl acetate/hexane to give the title compound (0.1 79 g) as solid. NMR (CDCl3+DMSO-δ6): 1.59 (s, 3H), 7.03 (t, 1H), 7.25 (t, 2H), 7.48 (brs, 1H), 7.64 (d, 2H), 7.78 (dd, 1H), 7.92 (m, 3H), 8.06 (d, 2H), 8.56 (d 1H), 9.72 (s, 1H), 9.9 (s, 1H); MS (ESP−): 525.

Workup

  1. customSolvent was then removed by evaporation
  2. customthe residue was partitioned between ethyl acetate (50 ml) and dilute aqueous hydrochloric acid (25 ml)
  3. extractionThe aqueous layer was further extracted with ethyl acetate (50 ml)
  4. washwashed with brine
  5. customdried
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by chromatography
  8. washeluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-aa562a61c60e4527bff6193ee5abc385
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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