1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 51000688, compound

HRID 571700Notes

Reaction equation

HRID 571700 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[N:42]1[C:47]2[NH:48][CH:49]=[CH:50][C:46]=2[C:45]([N:51]2[CH2:56][CH2:55][CH2:54][CH:53]([NH2:57])[CH2:52]2)=[N:44][CH:43]=1>CN(C=O)C.O.CCOC(C)=O>[N:42]1[C:47]2[NH:48][CH:49]=[CH:50][C:46]=2[C:45]([N:51]2[CH2:56][CH2:55][CH2:54][CH:53]([NH:57][C:9](=[O:11])[CH2:8][NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:52]2)=[N:44][CH:43]=1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66025N-PhenylglycineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67066694HCID 67066694, compound

Product 1

HCID 51000688HCID 51000688, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(phenylamino)acetic acid (37 mg, 0.25 mmol), EDCI (53 mg, 0.275 mmol), and HOBt (37 mg, 0.275 mmol) in DMF (1 mL) was DIEA (1.7 mL, 1.3 mg, 1.0 mmol) and 1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-amine (54 mg, 0.25 mmol). The solution was stirred at rt for several hours, diluted with water and EtOAc (1:1, 10 mL). The organic phase was separated, washed with brine, dried (Na2SO4) and concentrated in vacuo to afford a residue which was purified by reverse phase chromatography C 18 column and 10% acetonitrile/water containing 0.1% TFA to afford example 2. 1H NMR (400 MHz, DMSO-d6) δ 12.67 (s, 1H), 8.35 (s, 1H), 8.06 (d, J=6.8 Hz, 1H), 7.44 (s, 1H), 7.03˜7.70 (m, 3H), 6.52˜6.58 (m, 3H), 4.37 (d, J=12.7 Hz, 1H), 4.25 (d, J=12.2 Hz, 1H), 3.84 (s, 1H), 3.60 (m, 2H), 3.46 (m, 1H), 3.36 (m 1H), 1.87 (m, 2H), 1.61 (m, 2H). EIMS (m/z): calcd. for C19H22N6O (M++1) 351.2. found 351.2.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto afford a residue which
  6. customwas purified by reverse phase chromatography C 18 column and 10% acetonitrile/water containing 0.1% TFA
  7. customto afford example 2

Sources & evidence

ORD record
ord-e6570761d11147d4b9775e0416edaa39
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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