Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 60207462, compound

HRID 1192244Notes

Reaction equation

HRID 1192244 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:45][N:46]([CH3:60])[CH2:47][CH2:48][CH2:49][O:50][C:51]1[CH:57]=[CH:56][C:54]([NH2:55])=[CH:53][C:52]=1[O:58][CH3:59]>>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:55][C:54]2[CH:56]=[CH:57][C:51]([O:50][CH2:49][CH2:48][CH2:47][N:46]([CH3:60])[CH3:45])=[C:52]([O:58][CH3:59])[CH:53]=2)=[O:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

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 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acidHCID 60207419HCID 60207419, compound

Product 1

HCID 60207462HCID 60207462, compound

Procedure

Prepared according to the procedure described for example 70 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (250 mg, 0.71 mmol), 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (126 mg, 0.33 mmol) and 4-(3-dimethylaminopropoxy)-3-methoxy-aniline as in step B of 207 (298 mg, 0.78 mmol). The title compound was obtained as a yellow solid (50.0 mg, 13% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.45 (1H, s), 9.32 (1H, br), 9.01 (2H, m), 8.67 (1H, s), 7.33 (1H, m), 7.20 (1H, m), 4.02 (2H, m), 3.74 (3H, s), 3.21 (2H, m), 2.83 (6H, s), 2.07 (2H, m). MS m/z: 557.30, 559.29 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9064c1ed3dad4a5fa18f200e2f73e47c
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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