Hydrochloric Acid → HCID 66760331, compound

HRID 389502Notes

Reaction equation

CC1(C)[O:6][CH:5]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[N:17][C:16]([NH2:19])=[C:15]4[O:20][C:21]([C:23]5[CH:32]=[CH:31][CH:30]=[C:29]6[C:24]=5[CH:25]=[CH:26][N:27]=[CH:28]6)=[CH:22][C:14]=34)[CH:10]=[N:9]2)[CH2:4][O:3]1.CO.Cl>>[NH2:19][C:16]1[N:17]=[CH:18][C:13]([C:11]2[CH:10]=[N:9][N:8]([CH2:7][CH:5]([OH:6])[CH2:4][OH:3])[CH:12]=2)=[C:14]2[CH:22]=[C:21]([C:23]3[CH:32]=[CH:31][CH:30]=[C:29]4[C:24]=3[CH:25]=[CH:26][N:27]=[CH:28]4)[O:20][C:15]=12

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 53378068HCID 53378068, compound

Product 1

HCID 66760331HCID 66760331, compoundYield 4.4%

Procedure

4-{1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1H-pyrazol-4-yl}-2-(isoquinolin-5-yl)furo[2,3-c]pyridin-7-amine (25.0 mg, 0.0566 mmol) was dissolved in MeOH (0.5 mL, 10 mmol) and HCl (4 M in 1,4-dioxane, 0.30 mL, 1.2 mmol) was added. The reaction stirred at RT for 16 h. The product mixture was then concentrated in vacuo to a solid. Purification by flash chromatography (0 to 10% 7 N NH3/MeOH:EtOAc) afforded 1 mg (4%) of the title compound. 1H NMR (400 MHz, CD3OD) δ 9.35 (s, 1 H), 8.59 (d, J=6.06 Hz, 1 H), 8.51 (d, J=6.06 Hz, 1H), 8.37 (dd, J=7.33, 1.26 Hz, 1H), 8.26 (d, J=8.34 Hz, 1H), 8.12 (s, 1H), 7.94 (d, J=3.79 Hz, 2H), 7.81-7.89 (m, 1H), 7.54 (s, 1H), 4.40 (dd, J=14.02, 4.17 Hz, 1H), 4.19-4.27 (m, 1H), 4.01-4.12 (m, 1H), 3.52-3.61 (m, 2H); MS (ESI): 402.15 [M+H]+; HPLC tR=0.79 min (TOF: polar—3 min).

Workup

concentrationThe product mixture was then concentrated in vacuo to a solid
customPurification by flash chromatography (0 to 10% 7 N NH3/MeOH:EtOAc)

Sources & evidence

ORD record: ord-da9fc3a1796d44b2b3b3f7a3b51586ec
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

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