Cyclopropylamine → HCID 58459113, compound

HRID 2036671Notes

Reaction equation

HRID 2036671 reaction equation
C[CH2:2][N:3](C(C)C)C(C)C.[CH:10]1([NH2:13])[CH2:12][CH2:11]1.[NH2:14][C:15]1[N:20]=[CH:19][N:18]=[C:17]([NH:21][C@H:22]([C:24]2N(C3C=CC=CC=3)C3[C:35]([C:39]([OH:41])=O)=[CH:36][CH:37]=[CH:38][C:26]=3[N:25]=2)[CH3:23])[C:16]=1[C:42]#[N:43].C1CN([P+](ON2N=N[C:63]3[CH:64]=[CH:65][CH:66]=[CH:67][C:62]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:14][C:15]1[N:20]=[CH:19][N:18]=[C:17]([NH:21][C@H:22]([C:24]2[N:25]=[C:26]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([NH:13][CH:10]4[CH2:12][CH2:11]4)=[O:41])[N:3]3[C:2]=2[C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH3:23])[C:16]=1[C:42]#[N:43]

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 67433843HCID 67433843, compound

Product 1

HCID 58459113HCID 58459113, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of DIEA (0.062 mL, 0.356 mmol), cyclopropylamine (0.025 mL, 0.36 mmol), (S)-2-(1-(6-amino-5-cyanopyrimidin-4-ylamino)ethyl)-1-phenyl-1H-benzo[d]imidazole-7-carboxylic acid (0.071 g, 0.18 mmol), and PyBOP (0.185 g, 0.356 mmol) in DMF (1.18 mL) was stirred at rt for 1 h. The solution was loaded directly onto silica gel and purified by MPLC (eluted with 0-8% MeOH in DCM) to afford an off white solid that was repurified by MPLC (eluted with 0-100% (1:10:90 NH4OH:MeOH:DCM) solution in DCM) to afford 2-((1S)-1-((6-amino-5-cyano-4-pyrimidinyl)amino)ethyl)-N-cyclopropyl-3-phenylimidazo[1,2-a]pyridine-5-carboxamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.16-0.25 (m, 2H) 0.37-0.49 (m, 2H) 1.44 (d, J=6.65 Hz, 3H) 2.05 (tq, J=7.25, 3.64 Hz, 1H) 5.29 (quin, J=6.80 Hz, 1H) 6.84 (d, J=7.24 Hz, 1H) 6.94 (d, J=6.85 Hz, 1H) 7.12-7.51 (m, 8H) 7.75 (d, J=9.00 Hz, 1H) 7.95 (s, 1H) 8.67 (d, J=3.52 Hz, 1H). LC-MS (ESI) m/z 439.1 [M+H]+.

Workup

  1. custompurified by MPLC (eluted with 0-8% MeOH in DCM)
  2. customto afford an off white solid
  3. customthat was repurified by MPLC (eluted with 0-100% (1:10:90 NH4OH:MeOH:DCM) solution in DCM)

Sources & evidence

ORD record
ord-e447509eb3d441e291ac025bd3c94448
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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