Diisopropylethylamine → (1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-methyl-1H-indol-6-yl)(1,3-oxazinan-3-yl)methanone

HRID 630480Notes

Reaction equation

HRID 630480 reaction equation
ON1C2N=CC=CC=2N=N1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:19]=[N:20][C:21]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:33](O)=[O:34])[CH:31]=3)[C:26]([CH3:36])=[CH:25]2)=[N:22][CH:23]=1.[O:37]1[CH2:42][CH2:41][CH2:40][NH:39][CH2:38]1.C(N(C(C)C)CC)(C)C>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:19]=[N:20][C:21]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:33]([N:39]4[CH2:40][CH2:41][CH2:42][O:37][CH2:38]4)=[O:34])[CH:31]=3)[C:26]([CH3:36])=[CH:25]2)=[N:22][CH:23]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 2873641,3-OxazinaneHCID 1186662451-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-methyl-1H-indole-6-carboxylic acid

Product 1

HCID 118671765(1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-methyl-1H-indol-6-yl)(1,3-oxazinan-3-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDCxHCl (109 mg, 0.57 mmol) and 1-hydroxy-7-azabenzotriazole (17 mg, 0.12 mmol) were added to a solution of acid 89b) (200 mg, 0.50 mmol), 1,3-oxazinane (43.1 mg, 0.50 mmol) and diisopropylethylamine (0.13 mL, 0.74 mmol) in dichloromethane (2 mL) and the reaction mixture was stirred at room temperature for 18 h. The solvent was evaporated and the residue purified by column chromatography [silica, heptane with 5 to 100% ethyl acetate]. White solid. Yield: 51 mg. HPLC-MS: m/z [M+H]+=417.2

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography [silica, heptane with 5 to 100% ethyl acetate]

Sources & evidence

ORD record
ord-d85ea18ce22247b58dafdbfe25f54d63
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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