2'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-4'-yl 4-methylbenzenesulfonate → N4'-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazoline]-2',4'-diamine

HRID 2386995Notes

Reaction equation

HRID 2386995 reaction equation
CC1C=CC(S(O[C:12]2[C:21]3[CH2:20][CH2:19][CH2:18][C:17]4([CH2:25][CH2:24][CH2:23][CH2:22]4)[C:16]=3[N:15]=[C:14]([NH2:26])[N:13]=2)(=O)=O)=CC=1.Cl.Cl.[NH2:29][CH2:30][CH2:31][NH:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([NH2:39])[N:34]=1>>[NH2:39][C:35]1[N:34]=[C:33]([NH:32][CH2:31][CH2:30][NH:29][C:12]2[C:21]3[CH2:20][CH2:19][CH2:18][C:17]4([CH2:22][CH2:23][CH2:24][CH2:25]4)[C:16]=3[N:15]=[C:14]([NH2:26])[N:13]=2)[CH:38]=[CH:37][N:36]=1

Participants

3

Reactant 2

HCID 866343332'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-4'-yl 4-methylbenzenesulfonateHCID 86638141N4-(2-aminoethyl)pyrimidine-2,4-diamine dihydrochloride

Product 1

HCID 86638146N4'-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazoline]-2',4'-diamine

Procedure

The product from Example 10D (61 mg, 0.163 mmol) and the product from Example 1E (44 mg, 0.195 mmol) were treated under the conditions of Example 1F to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.41 (dd, J=11.19, 5.43 Hz, 2H) 1.47-1.57 (m, 2H) 1.57-1.69 (m, 4H) 1.69-1.83 (m, 2H) 1.96-2.09 (m, 2H) 2.16 (t, J=5.93 Hz, 2H) 3.33-3.52 (m, 4H) 5.45 (s, 2H) 5.66-5.77 (m, 1H) 5.84 (s, 2H) 6.20 (s, 1H) 6.89 (s, 1H) 7.61 (d, J=5.09 Hz, 1H); MS (ESI+) m/z 355.0 (M+H)+.

Sources & evidence

ORD record
ord-c76ca92b35344846aa290b38c9ccb57e
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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