Isopropylamine → HCID 18343691, compound

HRID 2301044Notes

Reaction equation

HRID 2301044 reaction equation
CN1CCOCC1.CN(C(O[N:16]1N=N[C:22]2[C:17]1=[CH:18]C=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:32][C:33]1[CH:38]=[C:37]([S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[C:48](O)=[O:49])(=[O:41])=[O:40])[CH:36]=[CH:35][C:34]=1[NH:51][C:52](=[O:60])[C@:53]([OH:59])([CH3:58])[C:54]([F:57])([F:56])[F:55].CC(N)C>C(Cl)Cl>[Cl:32][C:33]1[CH:38]=[C:37]([S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[C:48]([NH:16][CH:17]([CH3:22])[CH3:18])=[O:49])(=[O:40])=[O:41])[CH:36]=[CH:35][C:34]=1[NH:51][C:52](=[O:60])[C@:53]([OH:59])([CH3:58])[C:54]([F:56])([F:55])[F:57]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54493294HCID 54493294, compound

Product 1

HCID 18343691HCID 18343691, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Methylmorpholine (1.22 ml) and o-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.092 g) were added to a solution of (R)-N-[2-chloro-4-(2-carboxyphenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 125) (0.10 g) and 2-propylamine (0.024 ml) in DCM (20 ml) at (0° C. The reaction mixture was stirred at this temperature for 30 minutes then allowed to warm to room temperature, stirred for a further 3 hours then evaporated to dryness. The residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 50% ethyl acetate/hexane then triturated with ether/hexane to give the title compound (0.05 g) as a solid. NMR (CDCl3): 1.3 (d, 6H), 1.6 (s, 3H), 4.2-4.32 (m, 1H), 5.8 (brd, 1H), 7.4 (d, 1H), 7.5-7.7 (m, 3H), 7.9 (dd, 1H), 8.05-8.13 (m, 2H), 8.6 (d, 1H), 9.3 (brs, 1H); MS (ESP−): 491.

Workup

  1. stirringstirred for a further 3 hours
  2. customthen evaporated to dryness
  3. customThe residue was purified by chromatography on a silica gel Mega Bond Elut column
  4. washeluting with 50% ethyl acetate/hexane
  5. customthen triturated with ether/hexane

Sources & evidence

ORD record
ord-51a00d0929f24270b1e94df01692a0b1
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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