Dimethylformamide → HCID 90412113, compound

HRID 2175955Notes

Reaction equation

C(O[C:6]([N:8]1[C@@H:12]2[CH2:13][CH2:14][C@H:9]1[C@H:10]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH2:11]2)=[O:7])(C)(C)C.CC[N:25]([CH:29]([CH3:31])C)[CH:26]([CH3:28])C.CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=N[C:41]1=2)=[N+](C)C)C.[F:49][P-](F)(F)(F)(F)F.C[N:57]([CH:59]=O)C>>[F:49][C:43]1[CH:44]=[CH:45][C:28]([C:26]2[N:25]=[CH:29][CH:31]=[CH:59][N:57]=2)=[C:41]([C:6]([N:8]2[C@@H:12]3[CH2:13][CH2:14][C@H:9]2[C@H:10]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:11]3)=[O:7])[CH:42]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 90411649HCID 90411649, compound

Product 1

HCID 90412113HCID 90412113, compound

Procedure

To the title compound of Step B (50 mg, 0.18 mmol) in DMF (1.4 mL) was added DIPEA (0.078 mL, 0.45 mmol), intermediate A-7 (43 mg, 0.2 mmol) and HATU (75 mg, 0.2 mmol). Upon completion of the reaction, purification was performed using Agilent prep method A to give the title compound. MS (ESI) mass calcd. for C23H21FN4O2, 404.2. m/z found 405.2 [M+H]+. 1H NMR (CDCl3): 8.78 (d, J=4.9 Hz, 1H), 8.71 (d, J=4.8 Hz, 1H), 8.26-8.21 (m, 2H), 7.60-7.50 (m, 1H), 7.23-7.00 (m, 3H), 6.90-6.82 (m, 1H), 6.78-6.71 (m, 0.5H), 6.59-6.51 (m, 0.5H), 4.88-4.78 (m, 1H), 4.26-4.09 (m, 1H), 4.09-3.95 (m, 1H), 3.92-3.79 (m, 1H), 2.39-2.18 (m, 1H), 2.04-1.86 (m, 1H), 1.81-1.31 (m, 5H).

Workup

customUpon completion of the reaction, purification

Sources & evidence

ORD record: ord-853b5cfbec9743309154d16caa4b49c7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062078B2

Reaction notes

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