Triethylamine → HCID 44206502, compound

HRID 2094177Notes

Reaction equation

HRID 2094177 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][CH:24]2[CH2:26][CH2:25]2)=[C:8]([C:10]2[C:11]3[NH:18][CH:17]=[C:16]([C:19](O)=[O:20])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:9]=1)(=[O:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.[NH2:57][CH:58]1[CH2:63][CH2:62][N:61]([C:64](=[O:68])[C@@H:65]([OH:67])[CH3:66])[CH2:60][CH2:59]1>ClCCl>[OH:67][C@@H:65]([CH3:66])[C:64]([N:61]1[CH2:62][CH2:63][CH:58]([NH:57][C:19]([C:16]2[C:12]3[N:13]=[CH:14][N:15]=[C:10]([C:8]4[CH:9]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=[CH:6][C:7]=4[O:22][CH2:23][CH:24]4[CH2:25][CH2:26]4)[C:11]=3[NH:18][CH:17]=2)=[O:20])[CH2:59][CH2:60]1)=[O:68]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66866059HCID 66866059, compoundHCID 66867571HCID 66867571, compound

Product 1

HCID 44206502HCID 44206502, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-acetyl-2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid from example A81 (43 mg; 0.12 mmol) in dichloromethane (2 mL) is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.16 mmol), triethylamine (0.24 mmol) and 1-hydroxybenzotriazole (0.12 mmol). The suspension is stirred for 20 min at ambient temperature and then (S)-1-(4-amino-piperidin-1-yl)-2-hydroxy-propan-1-one hydrochloride from example A190 (0.16 mmol) is added. The reaction mixture is stirred overnight at ambient temperature. The volatiles are evaporated and the crude is distributed between ethyl acetate and aqueous phosphate buffer (1M, pH=7). The organic phase is separated, washed with aqueous phosphate buffer and evaporated to dryness. The obtained crude product is purified by preparative HPLC yielding 38 mg of the title compound as white solid.

Workup

  1. stirringThe reaction mixture is stirred overnight at ambient temperature
  2. customThe volatiles are evaporated
  3. customThe organic phase is separated
  4. washwashed with aqueous phosphate buffer
  5. customevaporated to dryness
  6. customThe obtained crude product
  7. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-5dc5ab2458d34415803ee79da9919af6
Source dataset
uspto-grants-2013_05
Patent number
US08445501B2

Reaction notes

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