tert-Butyl (3-aminopropyl)carbamate → tert-butyl 3-[(2-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl)amino]propylcarbamate

HRID 2386981Notes

Reaction equation

HRID 2386981 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].Cl[C:14]1[C:15]2[CH2:25][CH2:24][CH2:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:16]=2[N:17]=[C:18]([NH2:20])[N:19]=1>>[NH2:20][C:18]1[N:19]=[C:14]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[C:15]2[CH2:25][CH2:24][CH2:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:16]=2[N:17]=1

Participants

3

Reactant 2

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 866218984-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amine

Product 1

HCID 68603502tert-butyl 3-[(2-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl)amino]propylcarbamate

Procedure

tert-Butyl 3-aminopropylcarbamate (120 mg, 0.690 mmol) and the product from Example 1C (113 mg, 0.460 mmol) were treated under the conditions described in Example 1D to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.47 (s, 9H) 1.65-1.81 (m, 2H) 2.06-2.27 (m, 4H) 2.58 (t, J=6.74 Hz, 2H) 3.22 (q, J=5.95 Hz, 2H) 3.56 (q, J=6.08 Hz, 2H) 4.93 (s, 2H) 5.47-5.76 (m, 2H) 7.16-7.23 (m, 1H) 7.28-7.40 (m, 2H) 7.64-7.71 (m, 1H); MS (ESI+) m/z 384.1 (M+H)+.

Sources & evidence

ORD record
ord-8744bd3136e5426cbb7b8c839ea754a3
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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