[3-(Aminomethyl)oxetan-3-yl]methanamine → HCID 86691433, compound

HRID 540291Notes

Reaction equation

HRID 540291 reaction equation
C(O[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=2)[N:12]=[C:11]([N:22]2[CH2:28][C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[S:25](=[O:33])[CH2:24][CH2:23]2)[N:10]=1)C1C=CC=CC=1.[O:34]1[CH2:37][C:36]([CH2:40][NH2:41])([CH2:38][NH2:39])[CH2:35]1>>[NH2:39][CH2:38][C:36]1([CH2:40][NH:41][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=3)[N:12]=[C:11]([N:22]3[CH2:28][C:27]4[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=4[S:25](=[O:33])[CH2:24][CH2:23]3)[N:10]=2)[CH2:37][O:34][CH2:35]1

Participants

3

Reactant 2

HCID 10953471[3-(Aminomethyl)oxetan-3-yl]methanamineHCID 71255321HCID 71255321, compound

Product 1

HCID 86691433HCID 86691433, compound

Conditions

Temperature
170 °C

Procedure

A mixture of 4-(benzyloxy)-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4 (5H)-yl)quinazoline-6-carboxylic acid (170 mg, 0.37 mmol) and oxetane-3,3-diyldimethanamine (128 mg, 1.11 mmol) was heated at 170° C. for 30 minutes. Then the reaction mixture was cooled to room temperature and purified by preparative HPLC to afford 4-({[3-(Aminomethyl)oxetan-3-yl]methyl}amino)-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazoline-6-carboxylic acid, MS obsd. (ESI+) [(M+H)+] 468, 1H NMR (400 MHz, DMSO-d6) δ ppm 8.91-8.61 (m, 2 H), 8.09-8.00 (m, 1 H), 7.77-7.74 (m, 1 H), 7.68-7.65 (m, 1 H), 7.51-7.42 (m, 2 H), 7.27-7.13 (m, 1 H), 5.26-5.17 (m, 2 H), 4.89-4.68 (m, 4 H), 452-4.45 (m, 2 H), 4.40-4.31 (m, 2 H), 4.10-3.84 (m, 2 H), 3.20-3.01 (m, 2 H).

Workup

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-223e1ba1aca24d3a85e91a0f443e2214
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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