Sodium triacetoxyborohydride → N-(1-(4-(ethoxymethyl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

HRID 2175594Notes

Reaction equation

HRID 2175594 reaction equation
[CH2:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)[CH3:2].[NH:12]1[CH2:15][CH:14]([NH:16][C:17](=[O:34])[CH2:18][NH:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH2:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([N:12]2[CH2:13][CH:14]([NH:16][C:17](=[O:34])[CH2:18][NH:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([F:31])([F:33])[F:32])[CH:28]=4)[N:23]=[CH:22][N:21]=3)[CH2:15]2)[CH2:7][CH2:6]1)[CH3:2]

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 579490154-(Ethoxymethyl)cyclohexanoneHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Product 1

HCID 68004028N-(1-(4-(ethoxymethyl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Procedure

Reaction of 4-(ethoxymethyl)cyclohexanone with N-(azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide (as prepared in Example 1 Step G) in the presence of TEA and NaBH(OAc)3 as described in Example 1, Step H afforded the product. 1H NMR (ACETONITRILE-d3) δ: 0.79-1.04 (m, 2 H) 1.02-1.16 (m, 5 H) 1.22-1.39 (m, 8 H) 1.47 (d, J=4.04 Hz, 4 H) 1.66-1.79 (m, 1 H) 2.71 (t, J=7.33 Hz, 2 H) 3.14-3.21 (m, 3 H) 3.30-3.44 (m, 3 H) 3.48 (t, J=7.33 Hz, 2 H) 4.15 (d, J=5.81 Hz, 2 H) 4.23-4.39 (m, 1 H) 7.03 (br. s., 1 H) 7.33-7.47 (m, 1 H) 7.85-7.94 (m, 1 H) 7.98 (dd, J=8.84, 1.52 Hz, 1 H) 8.39 (s, 1 H) 8.59 (s, 1 H); ESI-MS (m/z): Calcd. For C23H30F3N5O2: 465.24. found: 466 (M+H).

Workup

  1. customafforded the product

Sources & evidence

ORD record
ord-d5686c36ccee4a6a8fc7b3ec71b568ce
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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