1,2-Dichloroethane → HCID 25108927, compound

HRID 2194640Notes

Reaction equation

HRID 2194640 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH2:32][CH:33]1[CH:40]2[CH2:41][C:36]3([CH2:43][OH:44])[CH2:37][CH:38]([CH2:42][CH:34]1[CH2:35]3)[CH2:39]2.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH:32][CH:33]2[CH:34]3[CH2:42][CH:38]4[CH2:37][C:36]([CH2:43][OH:44])([CH2:41][CH:40]2[CH2:39]4)[CH2:35]3)=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 18544082HCID 18544082, compoundHCID 579281674-Aminotricyclo[3.3.1.13,7]decane-1-methanol

Product 1

HCID 25108927HCID 25108927, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

3-Cyclohexylmethoxy-benzoic acid (300 mg, 1.3 mmol), HOBT (294 mg, 1.9 mmol), EDC (245 mg, 1.3 mmol), and 4-amino-1-hydroxymethyladamantane (232 mg, 1.28 mmol) were suspended in DMF (2.5 ml) before DIPEA (0.44 ml, 2.6 mmol) was added. The reaction mixture was stirred at 20° C. overnight. The reaction mixture was purified directly by Preparative HPLC to give 364 mg of the title compound as a mixture of two isomers. 1H NMR (400 MHz, CDCl3) δ: 7.29-7.34 (m, 2H), 7.21-7.26 (m, 1H), 6.98-7.04 (m, 1H), 3.79 (dd, 2H), 6.43 (dd, 1H), 4.10-4.25 (m, 1H), 3.79 (dd, 2H), 3.23 (d, 2H), 2.43 (s, 1H), 2.10-2.16 (m, 2H), 1.97-2.04 (m, 1H), 1.55-1.92 (m, 14H), 1.39-1.47 (m, 1H), 1.15-1.35 (m, 13H), 1.05 (q, 1H).

Workup

  1. additionwas added
  2. customThe reaction mixture was purified directly by Preparative HPLC

Sources & evidence

ORD record
ord-517f128b83254a0b88955ab6925b85a2
Source dataset
uspto-grants-2012_12
Patent number
US08334305B2

Reaction notes

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