Triethylamine → HCID 178521011, compound

HRID 931195Notes

Reaction equation

[F:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.[CH:14]1([C:17]2[N:22]=[C:21]([C:23]3[NH:40][C:26]4=[N:27][C:28]([N:31]5[CH2:36][CH2:35][CH2:34][C@@H:33]([C:37](O)=[O:38])[CH2:32]5)=[CH:29][CH:30]=[C:25]4[N:24]=3)[CH:20]=[CH:19][N:18]=2)[CH2:16][CH2:15]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH:14]1([C:17]2[N:22]=[C:21]([C:23]3[NH:40][C:26]4=[N:27][C:28]([N:31]5[CH2:36][CH2:35][CH2:34][C@@H:33]([C:37]([N:4]6[CH2:5][CH2:6][C@H:2]([F:1])[CH2:3]6)=[O:38])[CH2:32]5)=[CH:29][CH:30]=[C:25]4[N:24]=3)[CH:20]=[CH:19][N:18]=2)[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-3-Fluoropyrrolidine (175 μmol) was added to a vial followed by N,N-dimethylformamide (200 μL), triethylamine (35 μL, 250 μmol) and (R)-1-(2-(2-cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (200 μL, 50 μmol, 0.25 M in N,N-dimethylformamide) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HATU) (250 μL, 100 μmol, 0.4 M solution in N,N-dimethylformamide). The reaction mixture was shaken at 50° C. for 16 h. The solvent was evaporated by Speedvac and the residue was purified via preparative HPLC to afford the title compound. MS API-ES+ (M+H) 436; HPLC retention time 2.521 min (Method C).

Workup

customThe solvent was evaporated by Speedvac
customthe residue was purified via preparative HPLC

Sources & evidence

ORD record: ord-9f84eaf5dbec48c0a4e0feb4da466baf
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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