Diisopropylethylamine → 3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(3-hydroxycyclobutyl)benzamide

HRID 1049901Notes

Reaction equation

HRID 1049901 reaction equation
[NH2:1][C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([OH:17])=O)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.N[CH:22]1[CH2:25][CH2:24][CH:23]1[OH:26].C[N:28](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([NH:28][CH:25]3[CH2:24][CH:23]([OH:26])[CH2:22]3)=[O:17])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 124142992-Aminocyclobutan-1-olHCID 867039033-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)benzoic acid

Product 1

HCID 867039043-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(3-hydroxycyclobutyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same reaction and purification procedure, the acid 14 (90 mg, 0.34 mmol) was reacted with 2-aminocyclobutanol (CAS 4640-44-2) (59 mg, 0.68 mmol), HATU (145 mg, 0.38 mmol) and DIPEA (0.3 mL, 1.7 mmol) in DMF (1 mL) at room temperature to provide 3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(3-hydroxycyclobutyl)benzamide 15 as a mixture of cis and trans isomer. LC/MS (ESI+): m/z 336 (M+H). 1H NMR (400 MHz, DMSO) δ 8.80-8.66 (m, 2H), 8.61 (d, J=7.8 Hz, 1H), 8.56-8.47 (m, 1H), 8.43 (s, 1H), 8.19 (d, J=8.8 Hz, 1H), 8.06 (d, J=32.4 Hz, 2H), 8.01-7.91 (m, 1H), 7.63 (t, J=7.8 Hz, 1H), 5.12 (d, J=5.4 Hz, 1H), 5.03 (d, J=5.3 Hz, 1H), 4.50 (d, J=6.5 Hz, 1H), 4.37 (s, 1H), 4.03-3.81 (m, 2H), 2.95-2.78 (m, 1H), 2.62 (ddd, J=12.7, 11.7, 8.9 Hz, 1H), 2.40-2.27 (m, 1H), 2.20 (ddd, J=12.4, 8.0, 4.5 Hz, 1H), 1.97 (ddd, J=17.3, 8.6, 2.8 Hz, 2H).

Workup

  1. customthe same reaction and purification procedure

Sources & evidence

ORD record
ord-f36b9367afbe4936bb3eecfa872eb0b6
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

Loading…