Diisopropylethylamine → N-(4-(chlorodifluoromethoxy)phenyl)-6-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)-5-iodonicotinamide

HRID 924144Notes

Reaction equation

Cl[C:2]1[C:21]([I:22])=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[NH:23]1[CH2:27][C@@H:26]([OH:28])[C@H:25]([OH:29])[CH2:24]1.CCN(C(C)C)C(C)C>CC(O)C>[Cl:19][C:16]([F:18])([F:17])[O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:20]=[C:21]([I:22])[C:2]([N:23]3[CH2:27][C@@H:26]([OH:28])[C@H:25]([OH:29])[CH2:24]3)=[N:3][CH:4]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide (Stage 247.2, 300 mg, 0.654 mmol) and (3R,4R)-pyrrolidine-3,4-diol (88 mg, 0.850 mmol) in iPrOH (5 mL) was added DIPEA (0.228 mL, 1.307 mmol). The RM was stirred at 140° C. for 1 h and then 3 h at 130° C. The solvent was evaporated off under reduced pressure to give the crude product which was used directly without any further purification. UPLC-MS (Condition 3), tR=1.00 min, m/z=525.9/528.0 [M+H]+.

Workup

custom3 h
customat 130° C
customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record: ord-0b21ba1462f54fb2ae81f785c3048355
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278981B2

Reaction notes

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