Tetrahydrofuran → HCID 86585283, compound

HRID 2304755Notes

Reaction equation

HRID 2304755 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.CCN(C(C)C)C(C)C.CS(Cl)(=O)=O.[NH2:43][CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=1.C1C[O:54][CH2:53]C1>>[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:43]([CH2:44][C:45]2[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=2)[CH:53]=[O:54])=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 310183-PyridinemethanamineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 15922437HCID 15922437, compound

Product 1

HCID 86585283HCID 86585283, compound

Procedure

Following the procedure describing the preparation of example 166, 1-[(4-fluorophenyl)methyl]-3-(phenylmethoxy)indole-2-carboxylic acid (50 mg) in THF (3.0 mL) at 0° C. was treated with i-Pr2NEt (0.1 mL), MsCl (10 μL), stirred for 0.5 hours and then added 3-(aminomethyl)pyridine (20 mg). After work-up and purification by flash chromatography eluting with 30% EtOAc/hexanes the title amide (27.4 mg) was isolated as a light yellow oil.

Workup

  1. customAfter work-up and purification by flash chromatography
  2. washeluting with 30% EtOAc/hexanes the title amide (27.4 mg)
  3. customwas isolated as a light yellow oil

Sources & evidence

ORD record
ord-70926158ad1e4f08862d06046429f833
Source dataset
uspto-grants-2002_08
Patent number
US06436965B1

Reaction notes

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