Dimethylformamide → HCID 58362667, compound

HRID 2361498Notes

Reaction equation

HRID 2361498 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=[C:4]2[N:3]=1.Cl.Br[CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N([CH2:28][CH3:29])CC)C.CN(C=[O:34])C>>[N:3]1[C:4]2[N:5]([C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=2)[CH:6]=[CH:7][C:2]=1[N:20]1[CH2:21][CH2:22][CH:17]([CH2:29][CH2:28][OH:34])[CH2:18][CH2:19]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 58362356HCID 58362356, compoundHCID 66569497HCID 66569497, compound

Product 1

HCID 58362667HCID 58362667, compound

Procedure

To a microwave vial equipped with a magnetic stir bar, containing DMF (1 mL) was 2-bromobenzo[4,5]imidazo[1,2-a]pyrimidine (0.067 g, 0.27 mmol, 1.0 equiv), 4-bromopiperidine hydrochloride (0.099 g, 0.405 mmol, 1.5 equiv) and triethylamine (0.113 ml, 0.810 mmol, 3.0 equiv). The suspension was irradiated in a Biotage Initiator microwave reactor (250 W) at 100° C. for 10 min. After cooling to room temperature, the crude product was purified by HPLC to afford 0.06 g (67%) of T777P2 as a white solid. MS (ESI, Pos.) m/z: 332.1 (M+H)+

Workup

  1. customTo a microwave vial equipped with a magnetic stir bar
  2. customThe suspension was irradiated in a Biotage Initiator microwave reactor (250 W) at 100° C. for 10 min
  3. customthe crude product was purified by HPLC
  4. customto afford 0.06 g (67%) of T777P2 as a white solid

Sources & evidence

ORD record
ord-e61e6d724ba249d580722880e9b5f42c
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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