Diisopropylethylamine → (1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)((S)-2-(methoxyethyl)pyrrolidin-1-yl)methanone

HRID 630474Notes

Reaction equation

HRID 630474 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]1[CH:42]=[N:43][C:44]([N:47]2[C:55]3[C:50](=[CH:51][CH:52]=[C:53]([C:56]([OH:58])=O)[CH:54]=3)[C:49]([S:59]([CH3:61])=[O:60])=[CH:48]2)=[N:45][CH:46]=1.[CH3:62][O:63][CH2:64][C@@H]1CCCN1>CN(C=O)C>[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]1[CH:46]=[N:45][C:44]([N:47]2[C:55]3[C:50](=[CH:51][CH:52]=[C:53]([C:56]([N:15]4[CH2:14][CH2:13][CH2:12][C@H:10]4[CH2:11][CH2:62][O:63][CH3:64])=[O:58])[CH:54]=3)[C:49]([S:59]([CH3:61])=[O:60])=[CH:48]2)=[N:43][CH:42]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1186660891-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carboxylic acid

Product 1

HCID 118676905(1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)((S)-2-(methoxyethyl)pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (144 mg, 0.379 mmol, 1.5 eq) and diisopropylethylamine (0.13 mL, 0.759 mmol, 3.0 eq) were added at room temperature to a stirred solution of compound 51e) (100 mg, 0.253 mmol, 1.0 eq) and (S)-2-(methoxymethyl)pyrrolidine (0.02 mL, 0.303 mmol, 1.2 eq) in dry DMF (10 mL). The reaction mixture was stirred for 30 min and then diluted with ice water (20 mL). The precipitating solid was filtered off and dried. White solid. Yield: 110 mg (88% of theory). Melting range: 143-146° C. HPLC (method 1): Rt=10.03 min

Workup

  1. filtrationThe precipitating solid was filtered off
  2. customdried

Sources & evidence

ORD record
ord-04b0fd6b1e46487b960c4292c41f0bc8
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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