Hydrochloric Acid → HCID 67299188, compound

HRID 1958693Notes

Reaction equation

HRID 1958693 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:19][CH:18]=1.[F:31][C:32]1([F:47])[CH2:37][CH2:36][N:35]([C:38]2([C:44]([NH2:46])=[O:45])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:34][CH2:33]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl>C(Cl)Cl.CCN(CC)CC>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][C:12]([C:14]([N:41]2[CH2:40][CH2:39][C:38]([C:44]([NH2:46])=[O:45])([N:35]3[CH2:34][CH2:33][C:32]([F:31])([F:47])[CH2:37][CH2:36]3)[CH2:43][CH2:42]2)=[O:16])=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67187947HCID 67187947, compoundHCID 67299299HCID 67299299, compound

Product 1

HCID 67299188HCID 67299188, compoundYield 119.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

0.3 g of the compound obtained in stage 22A), 0.3 g of 4,4-difluoro-1,4′-bipiperidine-4′-carboxamide (described in Preparation 5, page 23, of Application WO 2008/068423), 0.45 ml of Et3N and 0.25 g of TBTU are added in order to 10 ml of CH2Cl2. After 3 hours at AT, the mixture is concentrated to dryness and the residue is taken up in AcOEt, washed with water, dried and concentrated to dryness. After purifying by chromatography on silica (elution gradient: CH2Cl2 up to CH2Cl2/MeOH 98/2), the compound obtained is dissolved in CH2Cl2, ethereal hydrochloric acid is added down to a pH of 1 and then the mixture is concentrated to dryness. 0.28 g of the expected compound is obtained.

Workup

  1. concentrationthe mixture is concentrated to dryness
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customAfter purifying by chromatography on silica (
  6. washelution gradient
  7. customCH2Cl2 up to CH2Cl2/MeOH 98/2), the compound obtained
  8. concentrationthe mixture is concentrated to dryness

Sources & evidence

ORD record
ord-f0ff4dd273954e44a47b04864aea8984
Source dataset
uspto-grants-2013_04
Patent number
US08410137B2

Reaction notes

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