Tetrahydrofuran → HCID 22254171, compound

HRID 1611708Notes

Reaction equation

HRID 1611708 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10]C2C=CN=C(N)C=2C#N)=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27].C([N:35]([CH2:37][C:38]([OH:40])=O)[CH3:36])(OC(C)(C)C)=O.C[N:42]([C:44](ON1N=NC2C=CC=CC1=2)=[N+:45](C)C)C.F[P-](F)(F)(F)(F)F.[CH:65]([N:68](CC)C(C)C)(C)C.O1[CH2:78][CH2:77][CH2:76][CH2:75]1>>[Cl:27][C:21]1[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=1[C:3]1[CH:4]=[C:5]([NH:8][CH2:9][CH2:10][NH:45][C:44]2[CH:78]=[CH:77][C:76]([C:65]#[N:68])=[CH:75][N:42]=2)[CH:6]=[CH:7][C:2]=1[NH:1][C:38](=[O:40])[CH2:37][NH:35][CH3:36]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131725263HCID 131725263, compound

Product 1

HCID 22254171HCID 22254171, compoundYield 93%

Procedure

To 20 mgs of 6-[(2-{[4-amino-3-(2,4-dichlorophenyl)phenyl]amino}ethyl)-aminopyridine-3-carbonitrile in tetrahydrofuran was added 19 mgs of BOC-sarcosine, 38 mgs of HBTU and 26.2 μl of N,N-diisopropylethylamine, and the mixture was stirred at room temperature over-night. After partitioning the mixture between ethyl acetate and water the organic layer was concentrated. To it was added dichloromethane and TFA to yield 1.2 mgs of 93% pure N˜1˜-[2′,4′-dichloro-5-({2-[(5-cyanopyridin-2-yl)amino]ethyl}amino)-1,1′-biphenyl-2-yl]-N˜2˜-methylglycinamide as the TFA salt after HPLC purification.

Workup

  1. customAfter partitioning the mixture between ethyl acetate and water the organic layer
  2. concentrationwas concentrated
  3. additionTo it was added dichloromethane and TFA

Sources & evidence

ORD record
ord-2e3bc016b57a4bf6a1868834d265dbaa
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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