Ammonium iodide → HCID 58424030, compound

HRID 2096423Notes

Reaction equation

[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=3)[O:16][CH:15](C3C=CC=CC=3)[CH2:14]2)[N:10]=[C:9]1SCC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:38].[I-].N.CO>CO.CCO>[NH2:38][C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:12](=[O:13])[C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=3)[O:16][CH:15]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:14]2)[N:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1′-benzyl-2′-(benzylthio)-6-bromo-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (60 mg, 0.10 mmol) in MeOH/EtOH (1:1, 2 mL) in a 10 mL CEM microwave test tube was added NH4I (50 mg, 0.34 mmol) and NH3/MeOH (7 N, 2 mL). The resulting mixture was heated in a CEM microwave reactor at 120° C. for 60 min. The cooled mixture was concentrated in vacuo and the residue was purified by reversed phase. HPLC to give 2′-amino-1′-benzyl-6-bromo-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (17.3 mg, 34%) as a TFA salt. MS m/z 462 (M+H+).

Workup

concentrationThe cooled mixture was concentrated in vacuo
customthe residue was purified by reversed phase

Sources & evidence

ORD record: ord-c9da0ffa54714d1ebb0873d65edc679a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450308B2

Reaction notes

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