Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 53482332, compound

HRID 2089329Notes

Reaction equation

HRID 2089329 reaction equation
[CH3:1][N:2]1[C:6]([N:7]2[CH2:12][CH2:11][CH2:10][C@H:9]([NH:13]C(=O)OC(C)(C)C)[CH2:8]2)=[C:5]([NH2:21])[CH:4]=[N:3]1.C(OC([NH:29][C:30]1[S:34][C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[F:41])=[N:32][C:31]=1[C:42](O)=[O:43])=O)(C)(C)C.CN(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[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[F:41])=[N:32][C:31]=1[C:42]([NH:21][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[N:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([NH2:13])[CH2:8]1)=[O:43]

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 58464983Carbamic acid, N-[(3S)-1-(4-amino-1-methyl-1H-pyrazol-5-yl)-3-piperidinyl]-, 1,1-dimethylethyl esterHCID 674367135-((Tert-butoxycarbonyl)amino)-2-(2-fluorophenyl)thiazole-4-carboxylic acid

Product 1

HCID 53482332HCID 53482332, compoundYield 13%

Procedure

Following the procedures as described in Example 113, (S)-tert-butyl 1-(1-methyl-4-amino-1H-pyrazol-5-yl)piperidin-3-ylcarbamate, 5-(tert-butoxycarbonylamino)-2-(2-fluorophenyl)thiazole-4-carboxylic acid, and HATU were reacted to give 107 as a white solid (36 mg, 13%) over two steps. 1H NMR (400 MHz, DMSO) δ 9.02 (s, 1H), 8.29 (dd, J=8.6, 7.0, 1H), 7.51-7.25 (m, 6H), 3.62 (d, J=13.9, 3H), 3.19-3.06 (m, 1H), 2.96 (dt, J=18.1, 10.4, 2H), 2.81 (d, J=9.0, 1H), 2.69 (dd, J=16.1, 7.5, 1H), 1.75 (dd, J=24.8, 8.7, 2H), 1.63-1.45 (m, 1H), 1.14 (dd, J=19.8, 9.2, 1H). ESIMS m/z=416.1 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-eb0aa33d4de04c10b46157a14bf3bac4
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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