Methanesulfonyl chloride → HCID 86585284, compound

HRID 2304756Notes

Reaction equation

HRID 2304756 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:10]2C(O)=O)=[CH:4][CH:3]=1.CC[N:31]([CH:35]([CH3:37])C)[CH:32]([CH3:34])C.CS(Cl)(=O)=[O:40].NCC1C=[CH:49][N:48]=[CH:47][CH:46]=1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:10]2[N:48]([CH2:47][C:46]2[CH:34]=[CH:32][N:31]=[CH:35][CH:37]=2)[CH:49]=[O:40])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 773174-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 15922437HCID 15922437, compound

Product 1

HCID 86585284HCID 86585284, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure describing the preparation of example 166, 1-[(4-fluorophenyl)methyl]-3-(phenylmethoxy)indole-2-carboxylic acid (50 mg) in THF (5.0 mL) at 0° C. was treated with i-Pr2NEt (0.1 mL), MsCl (10 μL) and after 0.5 hours 4-aminomethylpyridine (20 mg) was added to the reaction mixture. After work-up and purification by flash chromatography eluting with 20% EtOAc/hexanes the title amide (15 mg) was obtained as a light yellow oil.

Workup

  1. additionwas added to the reaction mixture
  2. customAfter work-up and purification by flash chromatography
  3. washeluting with 20% EtOAc/hexanes the title amide (15 mg)
  4. customwas obtained as a light yellow oil

Sources & evidence

ORD record
ord-2e9e870aa2cc481ab81039ebfd6a51c5
Source dataset
uspto-grants-2002_08
Patent number
US06436965B1

Reaction notes

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