1-Ethynylcyclopentanol → 9-[2-(1-Hydroxycyclopentyl)ethynyl]-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene-4-carboxamide

HRID 575132Notes

Reaction equation

HRID 575132 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][CH:10]([CH2:11]3)[N:9]3[C:5](=[N:6][C:7]([C:17]([NH2:19])=[O:18])=[CH:8]3)[C:4]=2[CH:3]=1.[C:20]([C:22]1([OH:27])[CH2:26][CH2:25][CH2:24][CH2:23]1)#[CH:21]>>[OH:27][C:22]1([C:20]#[C:21][C:2]2[CH:3]=[C:4]3[C:13](=[CH:14][CH:15]=2)[CH:12]2[CH2:16][CH:10]([CH2:11]2)[N:9]2[C:5]3=[N:6][C:7]([C:17]([NH2:19])=[O:18])=[CH:8]2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 870741-EthynylcyclopentanolHCID 8669308110-Bromo-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Product 1

HCID 866931579-[2-(1-Hydroxycyclopentyl)ethynyl]-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene-4-carboxamide

Procedure

9-Bromo-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7(12),8,10-pentaene-4-carboxamide (30 mg) was reacted with 1-ethynylcyclopentanol similar to as described in Procedure E to afford 8.9 mg of 9-[2-(1-hydroxycyclopentyl)ethynyl]-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene-4-carboxamide following reverse phase hplc purification. MS (Q1) 348 (M)+. 1H NMR (400 MHz, DMSO) δ 8.61 (d, J=11.1 Hz, 1H), 7.82 (s, 1H), 7.52 (s, 1H), 7.26 (s, 2H), 7.09 (s, 1H), 5.33 (s, 1H), 4.92 (q, J=4.5 Hz, 1H), 3.75-3.66 (m, 1H), 3.12-3.03 (m, 2H), 1.96-1.88 (m, 4H), 1.81-1.62 (m, 7H).

Sources & evidence

ORD record
ord-9260f70b8e4541c0b3da0f0473fe5f00
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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