Dimethylformamide → HCID 11387811, compound

HRID 641586Notes

Reaction equation

HRID 641586 reaction equation
O[C:2]([C:4]([F:7])([F:6])[F:5])=O.[CH:8]([N:11]([CH3:31])[C@@H:12]1[CH2:17][CH2:16][C@H:15]([NH2:18])[C@H:14]([CH2:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:13]1)([CH3:10])[CH3:9].C[N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.CN([P+](ON1N=N[C:52]2C=CC=[CH:56][C:51]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN([CH:69]=[O:70])C>>[CH:8]([N:11]([CH3:31])[C@@H:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:69](=[O:70])[CH2:34][C:35]2[O:36][C:37]3[C:2]([C:4]([F:7])([F:6])[F:5])=[CH:56][CH:51]=[CH:52][C:38]=3[N:33]=2)[C@H:14]([CH2:19][S:20]([C:23]2[CH:24]=[CH:25][C:26]([S:29][CH3:30])=[CH:27][CH:28]=2)(=[O:21])=[O:22])[CH2:13]1)([CH3:10])[CH3:9]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86595106HCID 86595106, compound

Product 1

HCID 11387811HCID 11387811, compound

Conditions

Temperature
0 °C

Procedure

(±)(1S*,2R*,4R*)-N4-Isopropyl-N4-methyl-2-(4-methylsulfanyl-benzenesulfonylmethyl)-cyclohexane-1,4-diamine TFA salt, from example (19 g), (65 mg) was dissolved in DMF (2 ml) prior to the addition of 4-methylmorpholine (74 μl) and example (22c) (39 mg). After cooling to 0° C., BOP reagent (77 mg) was added. The resulting mixture was warmed to rt and stirred overnight before being concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the title compound (28 mg). MS found: (M+H)+=598.5

Workup

  1. temperatureThe resulting mixture was warmed to rt
  2. concentrationbefore being concentrated
  3. customReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

Sources & evidence

ORD record
ord-f3cf83a7ac7d43ed9eaeec0398ccabbd
Source dataset
uspto-grants-2010_04
Patent number
US07696205B2

Reaction notes

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