1-Ethynyl-3-methylcyclohexan-1-ol → HCID 67280272, compound

HRID 16067Notes

Reaction equation

HRID 16067 reaction equation
[C:1]([C:3]1([OH:10])[CH2:8][CH2:7][CH2:6][CH:5]([CH3:9])[CH2:4]1)#[CH:2].[CH3:11][CH2:12][NH:13][C:14]([C@H:16]1[O:20][C@@H:19]([N:21]2[C:25]3[N:26]=[C:27](I)[N:28]=[C:29]([NH2:30])[C:24]=3[N:23]=[CH:22]2)[CH:18]([OH:32])[C@H:17]1[OH:33])=[O:15]>>[CH2:12]([NH:13][C:14]([CH:16]1[CH:17]([OH:33])[CH:18]([OH:32])[CH:19]([N:21]2[CH:22]=[N:23][C:24]3[C:25]2=[N:26][C:27]([C:2]#[C:1][C:3]2([OH:10])[CH2:8][CH2:7][CH2:6][CH:5]([CH3:9])[CH2:4]2)=[N:28][C:29]=3[NH2:30])[O:20]1)=[O:15])[CH3:11]

Participants

3

Reactant 2

HCID 2339171-Ethynyl-3-methylcyclohexan-1-olHCID 45039581(2S,3R,5R)-5-(6-Amino-2-iodo-9H-purin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide

Product 1

HCID 67280272HCID 67280272, compound

Procedure

The reaction of 1-Ethynyl-3-methyl-cyclohexanol (JR3149B) (100 mg, 0.72 mmol) with 2-iodo-NECA (25 mg, 0.06 mmol) under the general coupling conditions gave JR3179 (15.0 mg, 59%) as a white solid after purification by a silica plug and RP-HPLC. 1H NMR (CD3OD-d4) δ 8.49 (s, 1 H), 6.06 (d, J=6.9 Hz, 1 H), 4.75 (dd, J=6.4 Hz, J=4.9 Hz, 1 H), 4.46 (d, J=1.9 Hz, 1 H), 4.34 (dd, J=4.9 Hz, J=2.1 Hz, 1 H), 3.42 (m, 2 H), 2.09 (d, J=12.3 Hz, 2 H), 1.73 (m, 4 H), 1.46 (m, 1 H), 1.23 (m, 1 H), 1.16 9 (t, J=7.1 Hz, 3 H), 0.95 (d, J=6.2 Hz, 3 H), 0.89 (m, 1 H). 13C NMR (CD3OD-d4) δ. APCI m/z (rel intensity) 445.3 (MH+, 100), 427.4 (40), 254.4 (4).

Workup

  1. customgave JR3179 (15.0 mg, 59%) as a white solid
  2. customafter purification by a silica plug and RP-HPLC

Sources & evidence

ORD record
ord-4279e1beb2b24122923f4ff8966617a2
Source dataset
uspto-grants-2010_06
Patent number
US07737127B2

Reaction notes

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