Methylamine → HCID 25145099, compound

HRID 500195Notes

Reaction equation

HRID 500195 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:12]=[N:13][C:14]2[N:15]([C:17]([C:20]3([C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[CH:28][CH:27]=[CH:26]5)[CH2:22][CH2:21]3)=[CH:18][N:19]=2)[CH:16]=1)[C:5]([OH:7])=O.CN.F[P-](F)(F)(F)(F)F.[N:42]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:46]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.CO>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:12]=[N:13][C:14]2[N:15]([C:17]([C:20]3([C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[CH:28][CH:27]=[CH:26]5)[CH2:22][CH2:21]3)=[CH:18][N:19]=2)[CH:16]=1)[C:5]([NH:42][CH3:46])=[O:7]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67223924HCID 67223924, compound

Product 1

HCID 25145099HCID 25145099, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

3-Fluoro-4-(3-(1-(quinolin-6-yl)cyclopropyl)imidazo[1,2-a]pyrimidin-6-yl)benzoic acid obtained from Step 2 was dissolved in N,N-dimethylformamide (1 mL). To this solution was added methylamine (2M in THF, 0.2 mL), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (110 mg, 0.25 mmol) and N,N-diisopropylethylamine (0.12 mL, 0.68 mmol). The solution was stirred overnight at RT, diluted with MeOH, and purified by RP-HPLC (pH 10) to afford the desired compound. LCMS (M+H): m/z=438.0.

Workup

  1. custompurified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-81c8c6338bca453faf6f97001c74a6df
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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