Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 53482543, compound

HRID 2089338Notes

Reaction equation

HRID 2089338 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14]C(=O)OC(C)(C)C)[CH2:9][CH2:8]1.C(OC([NH:29][C:30]1[S:34][C:33]([C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])=[N:32][C:31]=1[C:43](O)=[O:44])=O)(C)(C)C.[CH3:46]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[NH2:29][C:30]1[S:34][C:33]([C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])=[N:32][C:31]=1[C:43]([NH:1][C:2]1[CH:3]=[N:4][N:5]([CH3:46])[C:6]=1[N:7]1[CH2:8][CH2:9][CH:10]([CH2:13][NH2:14])[CH2:11][CH2:12]1)=[O:44]

Participants

4

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acidHCID 86658422HCID 86658422, compound

Product 1

HCID 53482543HCID 53482543, compoundYield 21%

Procedure

Following the procedures as described in Example 113, tert-butyl (1-(4-amino-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate, 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid, and HATU were reacted to give 133 as a white solid (40 mg, 21%) over two steps. 1H NMR (400 MHz, DMSO) δ 8.76 (d, J=6.8, 1H), 7.62-7.38 (m, 4H), 7.38-7.16 (m, 2H), 3.63 (s, 3H), 3.15-2.94 (m, 5H), 2.88 (t, J=6.4, 1H), 1.86-1.60 (m, 2H), 1.42-1.05 (m, 3H). ESIMS m/z=448.1 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8d472ef3507349c8b2d5773c409f04b6
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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