Dimethylformamide → HCID 59625726, compound

HRID 2362046Notes

Reaction equation

[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:12][CH:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH2:10]2)=[O:8])=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=N[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]1=2)=[N+](C)C)C.[F:51][P-](F)(F)(F)(F)F.CN(C)[CH:60]=[O:61]>>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:12][CH:11]([N:13]3[CH2:18][CH2:17][N:16]([C:60]([C:43]4[CH:44]=[CH:45][C:46]([F:51])=[CH:47][CH:48]=4)=[O:61])[CH2:15][CH2:14]3)[CH2:10]2)=[O:8])=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 59625748HCID 59625748, compound

Product 1

HCID 59625726HCID 59625726, compound

Procedure

To a solution of compound 8f (100 mg, 0.3 mmol), compound 8g (44 mg, 0.31 mmol), and DIPEA (80 mg, 0.6 mmol) in dimethylformamide was added HBTU (141 mg, 0.37 mmol). After stirring for 18 h, the reaction was purified by preparative reverse phase HPLC to yield compound 299. 1H NMR (400 MHz, MeOD): δ 7.93-8.03 (m, 1H), 7.61-7.71 (m, 4H), 7.54-7.61 (m, 2H), 7.43-7.50 (m, 2H), 7.35-7.43 (m, 2H), 7.27-7.35 (m, 1H), 7.07-7.20 (m, 2H), 4.55-4.67 (m, 1H), 4.43-4.53 (m, 1H), 4.32-4.43 (m, 1H), 4.19-4.32 (m, 1H), 3.89-4.00 (m, 1H), 3.66-3.89 (m, 4H), 3.08 (br. s., 4H); MS m/z (M+H+) 444.2 (calculated for C27H26FN3O2, 443.53).

Workup

customthe reaction was purified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-743880cf48c349f09ca300151f419635
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691805B2

Reaction notes

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