Isopropylamine → HCID 178457677, compound

HRID 1982941Notes

Reaction equation

HRID 1982941 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[NH:24][C:23]5[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([OH:31])=O)[C:22]=5[N:21]=4)=[N:18][NH:17][C:14]3=[N:15][CH:16]=2)=[CH:3][N:2]=1.[CH:32]([NH2:35])([CH3:34])[CH3:33].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CS(C)=O.CO>[CH:32]([NH:35][C:29]([C:28]1[C:22]2[N:21]=[C:20]([C:19]3[C:13]4[C:14](=[N:15][CH:16]=[C:11]([C:4]5[C:5]6[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=6)[CH:1]=[N:2][CH:3]=5)[CH:12]=4)[NH:17][N:18]=3)[NH:24][C:23]=2[CH:25]=[CH:26][CH:27]=1)=[O:31])([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524258HCID 178524258, compound

Product 1

HCID 178457677HCID 178457677, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A mixture of Compound 17 (25 mg, 0.06 mmol), isopropylamine (11 μl, 0.12 mmol), HATU (23.4 mg, 0.06 mmol) and DIPEA (35 μl, 0.48 mmol) in DMSO (1 mL) was stirred at room temperature overnight. The solution was diluted with MeOH (0.4 mL) and purified by Gilson HPLC (10% to 90% of 0.1% TFA in ACN/0.1% TFA in H2O) to yield Compound 18 (9 mg, 33%) as a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ 9.79 (s, 1H), 8.96 (s, 1H), 8.84 (s, 1H), 8.78 (s, 1H), 8.57 (d, 1H, J=8.4 Hz), 8.16 (m, 2H), 8.04 (m, 1H), 7.87 (d, 1H, J=7.8 Hz), 7.69 (d, 1H, J=6.9 Hz), 7.32 (t, 1H, J=7.8 Hz), 3.99 (m, 1H), 0.86 (d, 6H, J=6 Hz); MS (ESI) m/z: 448 (M+H+).

Workup

  1. custompurified by Gilson HPLC (10% to 90% of 0.1% TFA in ACN/0.1% TFA in H2O)

Sources & evidence

ORD record
ord-aa7779f4834045c191aebd9e07808710
Source dataset
uspto-grants-2009_06
Patent number
US07541367B2

Reaction notes

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