tert-Butyl 3-acetylazetidine-1-carboxylate → 7-(Azetidin-3-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 64291

Reaction equation

HRID 64291 reaction equation
[C:1]([CH:4]1[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)(=O)[CH3:2].NC1NN=C(C2C=CC(OC3C=CC=CC=3)=CC=2)C=1C#N.NC1C=C(C2N3N=C(C4C=CC(OC5C=CC=CC=5)=CC=4)C(C#N)=C3N=CC=2)C=CC=1.ClCCC(NC1C=C(C2[N:84]3[N:85]=[C:86]([C:91]4[CH:96]=[CH:95][C:94]([O:97][C:98]5[CH:103]=[CH:102][CH:101]=[CH:100][CH:99]=5)=[CH:93][CH:92]=4)[C:87]([C:88]([NH2:90])=[O:89])=[C:83]3[NH:82][CH2:81]C2)C=CC=1)=O>>[NH:6]1[CH2:5][CH:4]([CH:1]2[N:84]3[N:85]=[C:86]([C:91]4[CH:96]=[CH:95][C:94]([O:97][C:98]5[CH:103]=[CH:102][CH:101]=[CH:100][CH:99]=5)=[CH:93][CH:92]=4)[C:87]([C:88]([NH2:90])=[O:89])=[C:83]3[NH:82][CH2:81][CH2:2]2)[CH2:7]1

Participants

5

Reactant 4

HCID 59841137tert-Butyl 3-acetylazetidine-1-carboxylateHCID 1176681877-(3-Aminophenyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrileHCID 1362142937-(3-(3-Chloropropanamido)phenyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamideHCID 178509389HCID 178509389, compound

Product 1

HCID 1369281387-(Azetidin-3-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

Procedure

The desired product was prepared from tert-butyl 3-acetylazetidine-1-carboxylate and 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile according to the procedures for 7-(3-aminophenyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (step 4 to 5), compound 2 (step 1 and 2) and compound 38 (step 2), under appropriate conditions recognized by one of ordinary skill in the art. 1H NMR (DMSO-d6) δ 8.70 (br s, 1H), 8.44 (br s, 111), 7.50 (d, J=8.6 Hz, 2H), 7.45-7.40 (m, 2H), 7.18 (t, J=7.6 Hz, 1H), 7.08 (d, J=7.4 Hz, 2H), 7.06 (d, J=8.6 Hz, 2H), 6.72 (br s, 1H), 4.46-4.38 (m, 1H), 4.24-4.15 (m, 1H), 4.07-3.94 (m, 3H), 3.29-3.24 (m, 2H), 3.19-3.10 (m, 1H), 2.13-2.04 (m, 1H), 1.78-1.69 (m, 1H). MS (ESI) m/e [M+1]+ 390.0.

Sources & evidence

ORD record
ord-43a19c583eb446a8aca87a5b4f3cbb4c
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Linked notes

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