2-Aminoadamantane hydrochloride → HCID 24744047, compound

HRID 1424588Notes

Reaction equation

HRID 1424588 reaction equation
Cl.[NH2:2][CH:3]1[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.C1N=CN([C:18]([N:20]2[CH:24]=N[CH:22]=[CH:21]2)=[O:19])C=1.CCN(C(C)C)C(C)C.N1CC[C:37]2([C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]([CH2:48][C:49]([OH:51])=[O:50])[CH2:40]2)[CH2:36]C1>C(Cl)Cl>[CH:10]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]([CH2:5]3)[CH:3]1[NH:2][C:18]([N:20]1[CH2:21][CH2:22][C:37]3([C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[CH:41]([CH2:48][C:49]([OH:51])=[O:50])[CH2:40]3)[CH2:36][CH2:24]1)=[O:19])[CH2:9]2

Participants

6

Reactant 4

HCID 253312-Aminoadamantane hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 53932726HCID 53932726, compound

Product 1

HCID 24744047HCID 24744047, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-aminoadamantane hydrochloride (120 mg, 0.64 mmol) and CDI (141 mg, 0.87 mmol) in anhydrous CH2Cl2 (4 mL) at 0° C. was added DIEA (374 mg, 2.90 mmol). The mixture was stirred at 0° C. for 1 h. A solution of compound 2-(2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (142 mg, 0.58 mmol) was added dropwise slowly. The mixture was stirred at rt overnight and concentrated to give the crude product. A portion of the crude product was purified by preparative HPLC to give 2-1′-((2-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (60 mg, 36%). 1H NMR: (400 MHz, CDCl3): δ=1.56-1.73 (m, 6H), 1.74-1.90 (m, 10H), 1.95 (m, 2H), 2.10 (m, 1H), 2.45 (m, 1H), 2.60 (m, 1H), 3.01 (m, 3H), 3.65 (m, 1H), 3.87-3.99 (m, 3H), 7.15-7.26 (m, 4H); LC-MS (4 min) tR=2.70 min, m/z=423 (M++1).

Workup

  1. stirringThe mixture was stirred at rt overnight
  2. concentrationconcentrated
  3. customto give the crude product
  4. customA portion of the crude product was purified by preparative HPLC
  5. customto give 2-1′-((2-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (60 mg, 36%)
  6. customLC-MS (4 min) tR=2.70 min, m/z=423 (M++1)

Sources & evidence

ORD record
ord-60ac28886d2745fc985dd653cdc91c56
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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