Azepane → HCID 59553057, compound

HRID 1170860Notes

Reaction equation

C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]1([N:19]2[C:27]3[CH2:26][CH2:25][CH2:24][CH:23]([CH2:28][C:29]([OH:31])=O)[C:22]=3[CH:21]=[N:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:32]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[C:13]1([N:19]2[C:27]3[CH2:26][CH2:25][CH2:24][CH:23]([CH2:28][C:29]([N:32]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[O:31])[C:22]=3[CH:21]=[N:20]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 45 °C

Procedure

CDI (63.2 mg, 0.39 mmol) is added to a solution of 2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)acetic acid (100 mg, 0.39 mmol) in CH2Cl2 (20 mL) cooled in an ice bath, and is heated to 45° C. for 2.5 hours. Then it is cooled to 0° C. and azacycloheptane (38.7 mg, 0.39 mmol) is added and is heated at 45° C. for 1 hour. The solvent is evaporated under reduced pressure, diluted in AcOEt and washed with diluted HCl. The organic phase is dried and evaporated under reduced pressure. The resulting crude product is purified by means of silica gel chromatography, giving 1-(2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)acetyl)azepane (45 mg, 0.13 mmol, 33%, oil).

Workup

temperaturecooled in an ice bath
temperatureThen it is cooled to 0° C.
temperatureis heated at 45° C. for 1 hour
customThe solvent is evaporated under reduced pressure
additiondiluted in AcOEt
washwashed with diluted HCl
customThe organic phase is dried
customevaporated under reduced pressure
customThe resulting crude product is purified by means of silica gel chromatography

Sources & evidence

ORD record: ord-54432b75e4234c448438c7eea5a72dfc
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829559B2

Reaction notes

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